Dye-forming coupler and silver halide color photographic light-sensitive material

ABSTRACT

A dye-forming coupler and compound of formula (I):  
                 
 
wherein Q represents a residue that forms, together with —N—C═N—, a nitrogen-containing 6-membered ring; R A  represents an aryl, heterocyclic, or —(R 1 ) r —(R 4 ) m  group; X represents an aryl group; Y represents a hydrogen atom, or a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent: 
wherein, 
 
when R A  represents an —(R 1 ) r —(R 4 ) m  group, R 1  represents a methylene group, a methine group, or a carbon atom; r is 1 to 30; R 4  represents a substituent except for a hydrogen atom; m is 1 to 30; and the —(R 1 ) r —(R 4 ) m  group does not represent a straight-chain alkyl group.

FIELD OF THE INVENTION

The present invention relates to a dye-forming coupler to form anazomethine dye, upon a coupling-reaction with an oxidized product of adeveloping agent. The present invention also relates to a silver halidephotographic light-sensitive material containing the coupler. Further,the present invention relates to an azomethine dye compound, which canbe produced by using the above-mentioned coupling reaction.

BACKGROUND OF THE INVENTION

In a silver halide photographic light-sensitive material (hereinaftersometimes referred to simply as “light-sensitive material”) forsubtractive color photography, a color image is formed by dyes of threeprimary colors of yellow, magenta and cyan. In the color photographythat uses the current p-phenylenediamine-series color-developing agent,an acylacetoanilide-series compound is used as a yellow coupler.However, the hue of the yellow dye obtained from the yellow coupler istinted with red, due to inferior sharpness at the foot portion of a peakin interest of the absorption curve at the longer wavelength side (thatis, on the absorption curve, the peak in interest has subsidiaryabsorption at its foot portion at the longer wavelength side), whichrenders it difficult to obtain a yellow hue of high-purity. Further,there is the problem that, due to the low molecular extinctioncoefficient of the yellow dyes, large amounts of both the coupler andsilver halide are needed to obtain a desired colored density. Therefore,sometimes it results in increasing film thickness of the light-sensitivematerial, and this consequently reduces the sharpness of the obtainedcolor image. Further, the above-mentioned yellow dyes, which are easilydecomposed under the conditions of high temperature and high humidity,or the conditions of light irradiation, have insufficient imagestability after development processing. Consequently, improvement ofthese problems is desired.

In order to solve such problems, the acyl group and the anilido groupwere improved. Recently, as improved couplers of the conventionalacylacetanilide-series, there are proposed, for example,1-alkylcyclopropanecarbonylacetanilide-series compounds, as described inJP-A-4-218,042 (“JP-A” means unexamined published Japanese patentapplication); cyclomalonic acid diamide-type couplers, as described inJP-A-5-11416; pyrrole-2 or 3-yl- or indole-2 or3-yl-carbonylacetanilide-series couplers, as described, for example, inEuropean Patent Nos. 953870A1, 953871A1, 953872A1, 953873A1, 953874A1and 953875A1. The dyes formed from these couplers were improved in termsof both hue and a molecular extinction coefficient, compared with theconventional ones. However, they are still deficient in image stability.Further, owing to their complicated chemical structure, the synthesisroute became longer, and consequently cost of the couplers becamehigher, causing a practical problem.

Further, U.S. Pat. No. 5,455,149 proposes acetoanilide-series couplersto which N-alkyl-4-pyrimidone is bonded. However, dyes obtained fromthese couplers are still inferior in hue, especially sharpness at thefoot portion of a peak of the absorption curve at the longer wavelengthside. Further, they are insufficient in fastness to light. Therefore,there is a need to improve these problems.

SUMMARY OF THE INVENTION

The present invention is a dye-forming coupler represented by thefollowing formula (I):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R_(A) represents an arylgroup, a heterocyclic group, or an —(R₁)_(r)—(R₄)_(m) group; Xrepresents an aryl group; Y represents a hydrogen atom, or a group thatis capable of being split-off upon a coupling reaction with an oxidizedproduct of a developing agent:wherein,when R_(A) represents an —(R₁)_(r)—(R₄)_(m) group, R₁ represents amethylene group, a methane group, or a carbon atom; r represents aninteger of 1 to 30, and R₁s may be the same or different independently,when r is 2 or more; R₄ represents a substituent except for a hydrogenatom; m represents an integer of 1 to 30, and R₄s may be the same ordifferent independently, or R₄s may be combined together to form amultiple bond, or alternatively R₄s may bond with each other to form aring, when m is 2 or more; and the —(R₁)_(r)—(R₄)_(m) group does notrepresent a straight-chain alkyl group.

Further, the present invention is a silver halide photographiclight-sensitive material, which comprises at least one dye-formingcoupler represented by the above formula (I).

Still further, the present invention is an azomethine dye compoundrepresented by the following formula (II):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R_(A) represents an arylgroup, a heterocyclic group, or an (R₁)_(r)—(R₄)_(m) group; X representsan aryl group:wherein,

-   when R_(A) represents an —(R₁)_(r)—(R₄)_(m) group, R₁ represents a    methylene group, a methine group, or a carbon atom; r represents an    integer of 1 to 30, and R₁s may be the same or different    independently, when r is 2 or more; R₄ represents a substituent    except for a hydrogen atom; m represents an integer of 1 to 30, and    R₄S may be the same or different independently, or R₄S may be    combine together to form a multiple bond, or alternatively R₄s may    bond with each other to form a ring, when m is 2 or more; and the    —(R₁)_(r)—(R₄)_(m) group does not represent a straight-chain alkyl    group;-   R₅ and R₆ each represent a hydrogen atom or a substituent, or R₅ and    R₆ may bond with each other to form a ring; R₇ represents a hydrogen    atom or a substituent; n represents 0 (zero) or an integer of 1 to    4, with the proviso that R₇S may be the same or different    independently, or R₇s may bond with each other to form a condensed    ring, when n is 2 or more; or R₇ may bond with R₅ or R₆ to form a    condensed ring, when n is 1 or more.

Other and further features and advantages of the invention will appearmore fully from the following description.

DETAILED DESCRIPTION OF THE INVENTION

According to the present invention, there is provided the followingmeans:(1) A dye-forming coupler represented by formula (I):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R_(A) represents an arylgroup, a heterocyclic group, or an (R₁)_(r)—(R₄)_(m) group; X representsan aryl group; Y represents a hydrogen atom, or a group that is capableof being split-off upon a coupling reaction with an oxidized product ofa developing agent:wherein,

-   when R_(A) represents an —(R₁)_(r)—(R₄)_(m) group, R₁ represents a    methylene group, a methine group, or a carbon atom; r represents an    integer of 1 to 30, and R₁s may be the same or different    independently, when r is 2 or more; R₄ represents a substituent    except for a hydrogen atom; m represents an integer of 1 to 30, and    R₄s may be the same or different independently, or R₄s may be    combined together to form a multiple bond, or alternatively R₄S may    bond with each other to form a ring, when m is 2 or more; and the    —(R)_(r)— (R₄)_(m) group does not represent a straight-chain alkyl    group.    (2) The dye-forming coupler according to the above item (1), wherein    the dye-forming coupler represented by formula (I) is represented by    formula (IA):    wherein Q represents a residue that forms, together with the —N—C═N—    moiety, a nitrogen-containing 6-membered ring; R₁₁ represents an    aryl group or a heterocyclic group; X represents an aryl group; Y    represents a hydrogen atom, or a group that is capable of being    split-off upon a coupling reaction with an oxidized product of a    developing agent.    (3) The dye-forming coupler according to the above item (2),    wherein, in the dye-forming coupler represented by formula (IA), Q    is a residue that forms, together with the —N—C═N—moiety, a    4-pyrimidone ring.    (4) The dye-forming coupler according to the above item (2),    wherein, in the dye-forming coupler represented by formula (IA), Q    is represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with    each other, to form, together with the —C═C— moiety, a 5- to    7-membered ring; or R₂ and R₃ each independently represent a    hydrogen atom or a substituent.    (5) The dye-forming coupler according to the above item (2),    wherein, in the dye-forming coupler represented by formula (IA), Q    is represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with    each other to form, together with the —C═C— moiety, a benzene ring.    (6) The dye-forming coupler according to the above item (1), wherein    the dye-forming coupler represented by formula (I) is represented by    the following formula (IB):    wherein Q represents a residue that forms, together with the —N—C═N—    moiety, a nitrogen-containing 6-membered ring; R₁ represents a    methylene group, a methine group, or a carbon atom; r represents an    integer of 1 to 30, and R₁s may be the same or different    independently, when r is 2 or more; R₄ represents a substituent    except for a hydrogen atom; m represents an integer of 1 to 30, and    R₄s may be the same or different independently, or R₄s may be    combined together to form a multiple bond, or alternatively R₄s may    bond with each other to form a ring, when m is 2 or more; X    represents an aryl group; Y represents a hydrogen atom, or a group    that is capable of being split-off upon a coupling reaction with an    oxidized product of a developing agent; and the-   —(R₁)_(r)—(R₄)_(m) group does not represent a straight-chain alkyl    group.    (7) The dye-forming coupler according to the above item (6),    wherein, in the dye-forming coupler represented by formula (IB), Q    is a residue that forms, together with the —N—C═N— moiety, a    4-pyrimidone ring.    (8) The dye-forming coupler according to the above item (6),    wherein, in the dye-forming coupler represented by formula (IB), Q    is represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with    each other, to form, together with the —C═C— moiety, a 5- to    7-membered ring; or R₂ and R₃ each independently represent a    hydrogen atom or a substituent.    (9) The dye-forming coupler according to the above item (6),    wherein, in the dye-forming coupler represented by formula (IB), Q    is represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with    each other, to form, together with the —C═C— moiety, a benzene ring.    (10) The dye-forming coupler according to any one of the above    items (6) to (9), wherein, in the dye-forming coupler represented by    formula (IB), R₄ is a group selected from the group consisting of an    alkyl group, an alkenyl group, an aryl group, a heterocyclic group,    a halogen atom, an amino group, a hydroxyl group, a carboxyl group,    a sulfo group, an acylamino group, an alkyl- or aryl-sulfonylamino    group, a carbamoyl group, a sulfamoyl group, an acyl group, a    sulfonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group,    an alkylthio group, an arylthio group, a cyano group, an alkoxy    group and an aryloxy group.    (11) The dye-forming coupler according to any one of the above    items (6) to (9), wherein, in the dye-forming coupler represented by    formula (IB), R₄ is a group selected from the group consisting of an    aryl group, an alkoxy group and an aryloxy group.    (12) The dye-forming coupler according to any one of the above    items (6) to (11), wherein, in the dye-forming coupler represented    by formula (IB), r is an integer of 1 to 6.    (13) The dye-forming coupler according to any one of the above    items (6) to (12), wherein, in the dye-forming coupler represented    by formula (IB), at least one R₄ bonds with a carbon atom at at    least one a- to i-positions in the (R₁)_(r).    (14) A silver halide photographic light-sensitive material,    comprising at least one dye-forming coupler represented by formula    (I):    wherein Q represents a residue that forms, together with the —N—C═N—    moiety, a nitrogen-containing 6-membered ring; R_(A) represents an    aryl group, a heterocyclic group, or an (R₁)_(r)—(R₄)_(m) group; X    represents an aryl group; Y represents a hydrogen atom, or a group    that is capable of being split-off upon a coupling reaction with an    oxidized product of a developing agent:    wherein,-   when R_(A) represents an —(R₁)_(r)—(R₄)_(m) group, R₁ represents a    methylene group, a methine group, or a carbon atom; r represents an    integer of 1 to 30, and R₁s may be the same or different    independently, when r is 2 or more; R₄ represents a substituent    except for a hydrogen atom; m represents an integer of 1 to 30, and    R₄S may be the same or different independently, or R₄s may be    combined together to form a multiple bond, or alternatively R₄s may    bond with each other to form a ring, when m is 2 or more; and the    —(R₁)_(r)—(R₄)_(m) group does not represent a straight-chain alkyl    group.    (15) The silver halide photographic light-sensitive material    according to the above item (14), wherein the dye-forming coupler    represented by formula (I) is represented by formula (IA):    wherein Q represents a residue that forms, together with the —N—C═N—    moiety, a nitrogen-containing 6-membered ring; R₁₁ represents an    aryl group or a heterocyclic group; X represents an aryl group; Y    represents a hydrogen atom, or a group that is capable of being    split-off upon a coupling reaction with an oxidized product of a    developing agent.    (16) The silver halide photographic light-sensitive material    according to the above item (15), wherein, in the dye-forming    coupler represented by formula (IA), Q is a residue that forms,    together with the —N—C═N— moiety, a 4-pyrimidone ring.    (17) The silver halide photographic light-sensitive material    according to the above item (15), wherein, in the dye-forming    coupler represented by formula (IA), Q is represented by    —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with each other, to    form, together with the —C═C— moiety, a 5- to 7-membered ring; or R₂    and R₃ each independently represent a hydrogen atom or a    substituent.    (18) The silver halide photographic light-sensitive material    according to the above item (15), wherein, in the dye-forming    coupler represented by formula (IA), Q is represented by    —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with each other, to    form, together with the —C═C— moiety, a benzene ring.    (19) The silver halide photographic light-sensitive material    according to the above item (14), wherein the dye-forming coupler    represented by formula (I) is represented by the following formula    (IB):    wherein Q represents a residue that forms, together with the —N—C═N—    moiety, a nitrogen-containing 6-membered ring; R₁ represents a    methylene group, a methine group, or a carbon atom; r represents an    integer of 1 to 30, and R₁s may be the same or different    independently, when r is 2 or more; R₄ represents a substituent    except for a hydrogen atom; m represents an integer of 1 to 30, and    R₄s may be the same or different independently, or R₄s may be    combined together to form a multiple bond, or alternatively R₄s may    bond with each other to form a ring, when m is 2 or more; X    represents an aryl group; Y represents a hydrogen atom, or a group    that is capable of being split-off upon a coupling reaction with an    oxidized product of a developing agent; and the —(R₁)_(r)—(R₄)_(m)    group does not represent a straight-chain alkyl group.    (20) The silver halide photographic light-sensitive material    according to the above item (19), wherein, in the dye-forming    coupler represented by formula (IB), Q is a residue that forms,    together with the —N—C═N— moiety, a 4-pyrimidone ring.

(21) The silver halide photographic light-sensitive material accordingto the above item (19), wherein, in the dye-forming coupler representedby formula (IB), Q is represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ andR₃ bond with each other, to form, together with the —C═C— moiety, a 5-to 7-membered ring; or R₂ and R₃ each independently represent a hydrogenatom or a substituent.

(22) The silver halide photographic light-sensitive material accordingto the above item (19), wherein, in the dye-forming coupler representedby formula (IB), Q is represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ andR₃ bond with each other, to form, together with the —C═C— moiety, abenzene ring.

(23) The silver halide photographic light-sensitive material accordingto any one of the above items (19) to (22), wherein, in the dye-formingcoupler represented by formula (IB), R₄ is a group selected from thegroup consisting of an alkyl group, an alkenyl group, an aryl group, aheterocyclic group, a halogen atom, an amino group, a hydroxyl group, acarboxyl group, a sulfo group, an acylamino group, an alkyl- oraryl-sulfonylamino group, a carbamoyl group, a sulfamoyl group, an acylgroup, a sulfonyl group, an alkoxycarbonyl group, an aryloxycarbonylgroup, an alkylthio group, an arylthio group, a cyano group, an alkoxygroup and an aryloxy group.

(24) The silver halide photographic light-sensitive material accordingto any one of the above items (19) to (22), wherein, in the dye-formingcoupler represented by formula (IB), R₄ is a group selected from thegroup consisting of an aryl group, an alkoxy group and an aryloxy group.

(25) The silver halide photographic light-sensitive material accordingto any one of the above items (19) to (24), wherein, in the dye-formingcoupler represented by formula (IB), r is an integer of 1 to 6.

(26) The silver halide photographic light-sensitive material accordingto any one of the above items (19) to (25), wherein, in the dye-formingcoupler represented by formula (IB), at least one R₄ bonds with a carbonatom at at least one α- to δ-positions in the (R₁)_(r).(27) An azomethine dye compound represented by formula (II):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R_(A) represents an arylgroup, a heterocyclic group, or an —(R₁)_(r)—(R₄)_(m) group; Xrepresents an aryl group:wherein,

-   when R_(A) represents an —(R₁)_(r)—(R₄)_(m) group, R₁ represents a    methylene group, a methine group, or a carbon atom; r represents an    integer of 1 to 30, and R₁s may be the same or different    independently, when r is 2 or more; R₄ represents a substituent    except for a hydrogen atom; m represents an integer of 1 to 30, and    R₄s may be the same or different independently, or R₄s may be    combine together to form a multiple bond, or alternatively R₄S may    bond with each other to form a ring, when m is 2 or more; and the    —(R₁)_(r)—(R₄)_(m) group does not represent a straight-chain alkyl    group; R₅ and R₆ each represent a hydrogen atom or a substituent, or    R₅ and R₆ may bond with each other to form a ring; R₇ represents a    hydrogen atom or a substituent; n represents o (zero) or an integer    of 1 to 4, with the proviso that R₇s may be the same or different    independently, or R₇s may bond with each other to form a condensed    ring, when n is 2 or more; or R₇ may bond with R₅ or R₆ to form a    condensed ring, when n is 1 or more.    (28) The azomethine dye compound according to the above item (27),    wherein the azomethine dye compound represented by formula (II) is    represented by the following formula (IIA):    wherein Q represents a residue that forms, together with the —N—C═N—    moiety, a nitrogen-containing 6-membered ring; R₁₁ represents an    aryl group or a heterocyclic group; X represents an aryl group; R₅    and R₆ each represent a hydrogen atom or a substituent, or R₅ and R₆    may bond with each other to form a ring; R₇ represents a hydrogen    atom or a substituent; n represents 0 (zero) or an integer of 1 to    4, with the proviso that R₇s may be the same or different    independently, or R₇S may bond with each other to form a condensed    ring, when n is 2 or more; or R₇ may bond with R₅ or R₆ to form a    condensed ring, when n is 1 or more.    (29) The azomethine dye compound according to the above item (28),    wherein, in the azomethine dye compound represented by formula    (IIA), Q is a residue that forms, together with the —N—C═N— moiety,    a 4-pyrimidone ring.

(30) The azomethine dye compound according to the above item (28),wherein, in the azomethine dye compound represented by formula (IIA), Qis represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with eachother, to form, together with the —C═C— moiety, a 5- to 7-membered ring;or R₂ and R₃ each independently represent a hydrogen atom or asubstituent.

(31) The azomethine dye compound according to the above item (28),wherein, in the azomethine dye compound represented by formula (IIA), Qis represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with eachother to form, together with the —C═C— moiety, a benzene ring.

(32) The azomethine dye compound according to the above item (27),wherein the azomethine dye compound represented by formula (II) isrepresented by the following formula (IIB):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R₁ represents a methylenegroup, a methine group, or a carbon atom; r represents an integer of 1to 30, and R₁s may be the same or different independently, when r is 2or more; R₄ represents a substituent except for a hydrogen atom; mrepresents an integer of 1 to 30, and R₄s may be the same or differentindependently, or R₄s may be combine together to form a multiple bond,or alternatively R₄s may bond with each other to form a ring, when m is2 or more; X represents an aryl group; and the —(R₁)_(r)—(R₄)_(m) groupdoes not represent a straight-chain alkyl group; R₅ and R₆ eachrepresent a hydrogen atom or a substituent, or R₅ and R₆ may bond witheach other to form a ring; R₇ represents a hydrogen atom or asubstituent; n represents 0 (zero) or an integer of 1 to 4, with theproviso that, R₇s may be the same or different independently, or R₇s maybond with each other to form a condensed ring, when n is 2 or more; orR₇s may bond with R₅ or R₆ to form a condensed ring, when n is 1 ormore.(33) The azomethine dye compound according to the above item (32),wherein, in the azomethine dye compound represented by formula (IIB), Qis a residue that forms, together with the —N—C═N— moiety, a4-pyrimidone ring.(34) The azomethine dye compound according to the above item (32),wherein, in the azomethine dye compound represented by formula (IIB), Qis represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with eachother, to form, together with the —C═C— moiety, a 5- to 7-membered ring;or R₂ and R₃ each independently represent a hydrogen atom or asubstituent.(35) The azomethine dye compound according to the above item (32),wherein, in the azomethine dye compound represented by formula (IIB), Qis represented by —C(—R₂)═C(—R₃)—CO—, in which R₂ and R₃ bond with eachother to form, together with the —C═C— moiety, a benzene ring.(36) The azomethine dye compound according to any one of the above items(32) to (35), wherein, in the azomethine dye compound represented byformula (IIB), R₄ is a group selected from the group consisting of analkyl group, an alkenyl group, an aryl group, a heterocyclic group, ahalogen atom, an amino group, a hydroxyl group, a carboxyl group, asulfo group, an acylamino group, an alkyl- or an aryl-sulfonylaminogroup, a carbamoyl group, a sulfamoyl group, an acyl group, a sulfonylgroup, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylthiogroup, an arylthio group, a cyano group, an alkoxy group and an aryloxygroup.(37) The azomethine dye compound according to any one of the above items(32) to (35), wherein, in the azomethine dye compound represented byformula (IIB), R₄ is a group selected from the group consisting of anaryl group, an alkoxy group and an aryloxy group.(38) The azomethine dye compound according to any one of the above items(32) to (37), wherein, in the azomethine dye compound represented byformula (IIB), r is an integer of 1 to 6.(39) The azomethine dye compound according to any one of the above items(32) to (38), wherein, in the azomethine dye compound represented byformula (IIB), at least one R₄ bonds with a carbon atom at at least oneα- to δ-positions in the (R₁)_(r).

The above-mentioned items (4), (5), (7) to (12), (17), (18), (20) to(25), (30), (31), and (33) to (38) are preferable embodiments of thepresent invention.

Herein, the dye-forming coupler represented by formula (IA) (e.g. thosedescribed in the above items (2) to (5)), and the light-sensitivematerial, which utilizes the compound of formula (IA), (e.g. thosedescribed in the above items (15) to (18)), and the azomethine dyecompound represented by formula (IIA), which is produced from thedye-forming coupler of formula (IA), (e.g. those described in the aboveitems (28) to (31)), are collectively referred to as a first embodimentof the present invention.

Further, herein, the dye-forming coupler represented by formula (IB)(e.g. those described in the above items (6) to (13)), and thelight-sensitive material, which utilizes the compound of formula (IB),(e.g. those described in the above items (19) to (26)), and theazomethine dye compound represented by formula (IIB), which is producedfrom the dye-forming coupler of formula (IB), (e.g. those described inthe above items (32) to (39)), are collectively referred to as a secondembodiment of the present invention.

Herein, the present invention means to include both the first embodimentand the second embodiment, unless otherwise specified.

The present invention is explained in detail below.

(Dye-Forming Coupler)

First, the compound represented by formula (IA) of the presentinvention, among the compound represented by the aforementioned formula(I) (herein they are also referred to as a dye-forming coupler) of thepresent invention are explained in detail.

In formula (IA), R₁₁ represents an aryl group or a heterocyclic group.

The aryl group is preferably a substituted or unsubstituted, andmonocyclic or condensed aryl group having 6 to 30 carbon atoms, e.g.,phenyl, p-tolyl, naphthyl, m-chlorophenyl, and o-hexadecanoylaminophenylgroups. The heterocyclic group is preferably a 5- to 7-memberedsubstituted or unsubstituted, saturated or unsaturated, aromatic ornon-aromatic, and monocyclic or condensed heterocyclic group having 3 to30 carbon atoms; more preferably a heterocyclic group havingring-constituting atoms selected from carbon, nitrogen and sulfur atoms,the heterocyclic group containing at least one hetero atom selected fromthe group consisting of a nitrogen atom, an oxygen atom and a sulfuratom; and furthermore preferably a 5- to 6-membered aromaticheterocyclic group; e.g., 2-furyl, 2-thienyl, 2-pyridyl, 4-pyridyl,2-pyrimidinyl, and 2-benzothiazolyl groups.

R₁₁ is preferably a phenyl group.

Examples of the substituent of the substituted aryl and the substitutedheterocyclic groups (i.e., the substituent that R₁₁ may have) include ahalogen atom, an alkyl group (including a cycloalkyl group and abicycloalkyl group), an alkenyl group (including a cycloalkenyl groupand a bicycloalkenyl group), an alkynyl group, an aryl group, aherocyclic group, a cyano group, a hydroxyl group, a nitro group, acarboxyl group, an alkoxy group, an aryloxy group, a silyloxy group, aheterocyclic oxy group, an acyloxy group, a carbamoyloxy group, analkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group(including an alkylamino group and an anilino group), an acylaminogroup, an aminocarbonylamino group, an alkoxycarbonylamino group, anaryloxycarbonylamino group, a sulfamoylamino group, an alkyl- or anaryl-sulfonylamino group, a mercapto group, an alkylthio group, anarylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfogroup, an alkyl- or aryl-sulfinyl group, an alkyl- or aryl-sulfonylgroup, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group,a carbamoyl group, an aryl- or heterocyclic-azo group, an imido group, aphosphino group, a phosphinyl group, a phosphinyloxy group, aphosphinylamino group and a silyl group.

In case where R₁₁ is substituted with two or more substituents, thesesubstituents may be the same or different independently, or thesubstituents adjacent to each other may combine together to form a ring,preferably a 5- to 6-membered, saturated or unsaturated ring.

The above-said substituent may be further substituted with asubstituent. Examples of the substituent are those as enumerated above.

Examples of the substituent which R₁₁ may have are further explainedbelow.

Examples of these substituents include a halogen atom (e.g., chlorine,bromine, iodine); an alkyl group (preferably a straight-chain orbranched-chain and substituted or unsubstituted alkyl group, morepreferably the alkyl group having 1 to 30 carbon atoms, e.g., methyl,ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl,2-cyanoethyl, 2-ethylhexyl); a cycloalkyl group (preferably asubstituted or unsubstituted monocyclic cycloalkyl group having 3 to 30carbon atoms, e.g., cyclohexyl, cyclopentyl, and 4-n-dodecyl cyclohexyl,and a polycycloalkyl group including groups composed of a polycyclicstructure such as a bicycloalkyl group (preferably a substituted orunsubstituted bicycloalkyl group having 5 to 30 carbon atoms, e.g.,bicyclo[1,2,2]heptane-2-yl and bicyclo[2,2,2]octane-3-yl), and atricycloalkyl group; more preferably a monocycloalkyl group orbicycloalkyl group and particularly preferably a monocyclic cycloalkylgroup); an alkenyl group (preferably a straight-chain or branched-chain,and substituted or unsubstituted alkenyl group, more preferably thealkenyl group having 2 to 30 carbon atoms, e.g., vinyl, allyl, prenyl,geranyl, oleyl); a cycloalkenyl group (preferably a substituted orunsubstituted cycloalkenyl group having 3 to 30 carbon atoms, e.g.,2-cyclopentene-1-yl, and 2-cyclohexene-1-yl; and a polycycloalkenylgroup such as a bicycloalkenyl group (preferably a substituted orunsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, e.g.,bicyclo[2,2,1]hepto-2-ene-1-yl and bicyclo[2,2,2]octo-2-ene-4-yl) and atricycloalkenyl group, with a monocyclic cycloalkenyl group beingparticularly preferred); an alkynyl group (preferably a substituted orunsubstituted alkynyl group having 2 to 30 carbon atoms, e.g., ethynyl,propargyl, trimethylsilylethynyl); an aryl group (preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms,e.g., phenyl, p-tolyl, naphthyl, m-chlorophenyl,o-hexadecanoylaminophenyl); a heterocyclic group (preferably a 5- to7-membered substituted or unsubstituted, saturated or unsaturated,aromatic or non-aromatic, and monocyclic or condensed heterocyclicgroup, more preferably a heterocyclic group having ring-constitutingatoms selected from carbon, nitrogen and sulfur atoms, the heterocyclicgroup containing at least one hetero atom selected from the groupconsisting of nitrogen, oxygen and sulfur atoms; furthermore preferablya 5- to 6-membered aromatic heterocyclic group having 3 to 30 carbonatoms, e.g., 2-furyl, 2-thienyl, 2-pyridyl, 4-pyridyl, 2-pyrimidinyl,2-benzothiazolyl); a cyano group; a hydroxyl group; a nitro group; acarboxyl group; an alkoxy group (preferably a substituted orunsubstituted alkoxyl group having 1 to 30 carbon atoms, e.g., methoxy,ethoxy, isopropoxy, t-butoxy, n-octyloxy, 2-methoxyethoxy); an aryloxygroup (preferably a substituted or unsubstituted aryloxy group having 6to 30 carbon atoms, e.g., phenoxy, 2-methylphenoxy, 4-t-buthylphenoxy,3-nitrophenoxy, 2-tetradecanoylaminophenoxy); a silyloxy group(preferably a silyloxy group having 3 to 20 carbon atoms, e.g.,trimethylsilyloxy, t-butyldimethylsilyloxy); a herocyclic oxy group(preferably a substituted or unsubstituted heterocyclic oxy group having2 to 30 carbon atoms, more preferably those having the heterocyclicmoiety as described to explain the above-mentioned heterocyclic group,e.g., 1-phenyltetrazole-5-oxy, 2-tetrahydropyranyloxy); an acyloxy group(preferably formyloxy, a substituted or unsubstituted alkylcarbonyloxygroup having 2 to 30 carbon atoms or a substituted or unsubstitutedarylcarbonyloxy group having 6 to 30 carbon atoms, e.g., formyloxy,acetyloxy, pivaloyloxy, stealoyloxy, benzoyloxy,p-methoxyphenylcarbonyloxy); a carbamoyloxy group (preferably asubstituted or unsubstituted carbamoyloxy group having 1 to 30 carbonatoms, e.g., N,N-dimethylcarbamoyloxy, N,N-diethylcarbamoyloxy,morpholinocarbonyloxy, N,N-di-n-octylaminocarbonyloxy,N-n-octylcarbamoyl oxy); an alkoxycarbonyloxy group (preferably asubstituted or unsubstituted alkoxycarbonyloxy group having 2 to 30carbon atoms, e.g., methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, n-octylcarbonyloxy); an aryloxycarbonyloxy group(preferably a substituted or unsubstituted aryloxycarbonyloxy grouphaving 7 to 30 carbon atoms, e.g., phenoxycarbonyloxy,p-methoxyphenoxycarbonyloxy, p-n-hexadecyloxyphenoxycarbonyloxy); anamino group (preferably an unsubstituted amino group, a substituted orunsubstituted alkylamino group having 1 to 30 carbon atoms, asubstituted or unsubstituted arylamino group having 6 to 30 carbonatoms, and a heterocyclic amino group having 0 (zero) to 30 carbonatoms, e.g., amino, methylamino, dimethylamino, anilino,N-methyl-anilino, diphenylamino, N-1,3,5-triazine-2-il amino); anacylamino group (preferably a formylamino group, a substituted orunsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, anda substituted or unsubstituted arylcarbonylamino group having 6 to 30carbon atoms, e.g., formylamino, acetylamino, pivaloylamino,lauroylamino, benzoylamino, and3,4,5-tri-n-octyloxyphenylcarbonylamino); an aminocarbonylamino group(preferably a substituted or unsubstituted aminocarbonylamino grouphaving 1 to 30 carbon atoms, e.g., carbamoylamino,N,N-dimethylaminocarbonylamino, N,N-diethylamino carbonylamino,morpholinocarbonylamino); an alkoxycarbonylamino group (preferably asubstituted or unsubstituted alkoxycarbonylamino group having 2 to 30carbon atoms, e.g., methoxycarbonylamino, ethoxycarbonylamino,t-butoxycarbonylamino, n-octadecyloxycarbonylamino,N-methyl-methoxycarbonylamino); an aryloxycarbonylamino group(preferably a substituted or unsubstituted aryloxycarbonylamino grouphaving 7 to 30 carbon atoms, e.g., phenoxycarbonylamino,p-chlorophenoxycarbonylamino, m-n-octyloxyphenoxycarbonyl amino); asulfamoyl amino group (preferably a substituted or unsubstitutedsulfamoylamino group having 0 (zero) to 30 carbon atoms, e.g.,sulfamoylamino, N,N-dimethylaminosulfonylamino, N-n-octylaminosulfonylamino); an alkyl- or aryl-sulfonylamino group (preferably asubstituted or unsubstituted alkyl sulfonylamino group having 1 to 30carbon atoms and a substituted or unsubstituted aryl sulfonylamino grouphaving 6 to 30 carbon atoms, e.g., methyl sulfonylamino,butylsulfonylamino, phenylsulfonylamino,2,3,5-trichlorophenylsulfonylamino, p-methylphenylsulfonylamino); amercapto group; an alkylthio group (preferably a substituted orunsubstituted alkylthio group having 1 to 30 carbon atoms, e.g.,methylthio, ethylthio, n-hexadecylthio); an arylthio group (preferably asubstituted or unsubstituted arylthio group having 6 to 30 carbon atoms,e.g., phenylthio, p-chlorophenylthio, m-methoxyphenylthio); aheterocyclic thio group (preferably a substituted or unsubstitutedheterocyclic thio group having 2 to 30 carbon atoms in which theheterocyclic moiety is preferably the same as that of theabove-described heterocyclic group, e.g., 2-benzothiazolylthio,1-phenyltetrazol-5-ylthio); a sulfamoyl group (preferably a substitutedor unsubstituted sulfamoyl group having 0 (zero) to 30 carbon atoms,e.g., N-ethylsulfamoyl, N-(3-dodecyloxypropyl)sulfamoyl,N,N-dimethylsulfamoyl, N-acetylsulfamoyl, N-benzoylsulfamoyl,N-(N′-phenylcarbamoyl)sulfamoyl); a sulfo group; an alkyl- oraryl-sulfinyl group (preferably a substituted or unsubstitutedalkylsulfinyl group having 1 to 30 carbon atoms and a substituted orunsubstituted arylsulfinyl group having 6 to 30 carbon atoms, e.g.,methylsulfinyl, ethylsulfinyl, phenylsulfinyl, p-methylphenylsulfinyl);an alkyl- or aryl-sulfonyl group (preferably a substituted orunsubstituted alkylsulfonyl group having 1 to 30 carbon atoms and asubstituted or unsubstituted arylsulfonyl group having 6 to 30 carbonatoms, e.g., methylsulfonyl, ethylsulfonyl, phenylsulfonyl,p-methylphenylsulfonyl); an acyl group (preferably a formyl group, asubstituted or unsubstituted alkylcarbonyl group having 2 to 30 carbonatoms and a substituted or unsubstituted arylcarbonyl group having 7 to30 carbon atoms, e.g., acetyl, pivaloyl, 2-chloroacetyl, stearoyl,benzoyl, p-n-octyloxyphenylcarbonyl); an aryloxycarbonyl group(preferably a substituted or unsubstituted aryloxycarbonyl group having7 to 30 carbon atoms, e.g., phenoxycarbonyl, o-chlorophenoxycarbonyl,m-nitrophenoxycarbonyl, p-t-butylphenoxycarbonyl); an alkoxycarbonylgroup (preferably a substituted or unsubstituted alkoxycarbonyl grouphaving 2 to 30 carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl,t-butoxycarbonyl, n-octadecyloxycarbonyl); a carbamoyl group (preferablya substituted or unsubstituted carbamoyl group having 1 to 30 carbonatoms, e.g., carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl,N,N-di-n-octylcarbamoyl, N-(methylsulfonyl)carbamoyl); an aryl- orheterocyclic-azo group (preferably a substituted or unsubstituted arylazo group having 6 to 30 carbon atoms, and a substituted orunsubstituted heterocyclic azo group having 3 to 30 carbon atoms inwhich the heterocyclic part is preferably the same as that of theabove-described heterocyclic group, e.g., phenylazo, p-chlorophenylazo,5-ethylthio-1,3,4-thiadiazole-2-yl azo); an imido group (preferably asubstituted or unsubstituted imido group having 2 to 30 carbon atoms,e.g., N-succinimido, N-phthalimido); a phosphino group (preferably asubstituted or unsubstituted phosphino group having 2 to 30 carbonatoms, e.g., dimethylphosphino, diphenylphosphino,methylphenoxyphosphino); a phosphinyl group (preferably a substituted orunsubstituted phosphinyl group having 2 to 30 carbon atoms, e.g.,phosphinyl, dioctyloxyphosphinyl, diethoxyphosphinyl); a phosphinyloxygroup (preferably a substituted or unsubstituted phosphinyloxy grouphaving 2 to 30 carbon atoms, e.g., diphenoxyphosphinyloxy,dioctyloxyphosphinyloxy); a phosphinylamino group (preferably asubstituted or unsubstituted phosphinylamino group having 2 to 30 carbonatoms, e.g., dimethoxyphosphinylamino, dimethylaminophosphinylamino);and a silyl group (preferably a substituted or unsubstituted silyl grouphaving 3 to 30 carbon atoms, e.g., trimethylsilyl, t-butyldimethylsilyl,phenyldimethylsilyl).

Among the substituents that R₁₁ may additionally have, a hydrogenatom(s) in the substituents may be replaced with the above-describedgroup. Examples of these groups that R₁₁ may additionally have includean alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group,an alkylsulfonylaminocarbonyl group, and an arylsulfonyl aminocarbonylgroup. As the specific examples, methylsulfonylaminocarbonyl,p-methylphenylsulfonylaminocarbonyl, acetylaminosulfonyl,benzoylaminosulfonyl, ethylcarbonylaminosulfonyl,isopropylcarbonylaminosulfonyl,p-methanesulfonylphenylcarbonylaminosulfonyl,dodecylsulfonylaminocarbonyl, and p-chlorophenylsulfonylaminocarbonylgroup are enumerated.

Further, the substituents adjacent to each other may combine together toform a ring, preferably a 5- to 7-membered saturated or unsaturatedring, and the ring may be alicyclic, aromatic or heterocyclic ring. As aexample of the ring, benzene, furan, thiophene, cyclopentane, andcyclohexane rings are enumerated.

Each of these substituents and the rings that are formed by bonding ofthese substituents with each other, may further have a substituentthereon, such as those enumerated as the substituent that theabove-mentioned R₁₁ may have.

The total carbon atom of the substituent that the aryl group or theheterocyclic group of R₁₁ may have, is preferably 2 to 50, morepreferably 8 to 45, and furthermore preferably 15 to 40.

Preferred example of these substituents is an alkyl group, an alkenylgroup, an aryl group, a heterocyclic group, a halogen atom, an alkoxygroup, an aryloxy group, an alkylthio group, an arylthio group, a cyanogroup, an acylamino group, an alkyl- or aryl-sulfonylamino group, analkoxycarboxyl group, a carbamoyl group, a sulfamoyl group, analkylamino group or an arylamino group.

In formula (IA), Q represents a residue that forms, together with the—N—C═N— moiety, a nitrogen-containing 6-membered heterocyclic ring. Thenitrogen-containing heterocyclic ring is a substituted or unsubstitutedheterocyclic ring, more preferably a heterocyclic ring composed of acarbon atom and a nitrogen atom, as ring-forming atoms, and having 2 to4 nitrogen atoms; furthermore preferably a nitrogen-containing6-membered heterocyclic ring having 2 to 30 carbon atoms and 2 nitrogenatoms. Examples of the nitrogen-containing 6-membered ring that isformed by Q together with the —N—C═N— moiety, include 4-pyrimidone,1,3-diazine-4,6-dione, 1,3,5-triazine-2-one and 1,2,4-triazine-5-one.The nitrogen-containing 6-membered ring that is formed by Q togetherwith the —N—C═N— moiety, may have a substituent. Examples of thesubstituent are the same as those of the substituent, which theabove-mentioned R₁₁ may have.

Further, the substituents adjacent to each other may combine together toform a ring, and a 5- to 7-membered saturated or unsaturated ring ispreferable. The ring may be alicyclic, aromatic or heterocyclic ring. Asexample of the ring, benzene, furan, thiophene, cyclopentane, andcyclohexane rings are enumerated.

Each of the above-mentioned substituents and the rings that are formedby combination of some of these substituents, also may have asubstituent. Examples of the substituent are the same as those of thesubstituent, which the above-mentioned R₁₁ may have.

The total carbon atoms of the above-mentioned substituent is preferably2 to 50, more preferably 8 to 45, furthermore preferably 15 to 40.

Preferred of these substituents are an alkyl group, an alkenyl group, anaryl group, a heterocyclic group, a halogen atom, an alkoxy group, anaryloxy group, an alkylthio group, an arylthio group, a cyano group, anacylamino group, an alkyl- and aryl-sulfonylamino group, analkoxycarboxyl group, a carbamoyl group, a sulfamoyl group, analkylamino group and an arylamino group.

Q is preferably a residue that forms, together with the —N—C═N— moiety,a 4-pyrimidone ring. More preferably Q is represented by—C(—R₂)═C(—R₃)—CO—. R₂ and R₃, when combined with each other, forms,together with the —C═C-moiety, a 5- to 7-membered ring, or R₂ and R₃each independently represent a hydrogen atom or a substituent. The ringthat is formed by combination of R₂ and R₃ together with the —C═C—moiety, is preferably a 5- to 7-membered alicyclic, aromatic orheterocyclic ring. As example of the ring, benzene, pyrazole, furan,thiophene, cyclopentene and cyclohexene rings are enumerated. Morepreferably the ring is 6-membered aromatic ring. A benzene ring is mostpreferred.

When R₂ and R₃ each represent a substituent, R₂ and R₃ may be the sameor different independently. Examples of the substituent are the same asthose of the substituent, which the above-mentioned R₁₁ may have.

In formula (IA), X represents an aryl group. The aryl group ispreferably a substituted or unsubstituted aryl group having 6 to 30carbon atoms, such as a phenyl group and a naphthyl group. X may have asubstituent. Examples of the substituent are the same as those of thesubstituent, which the above-mentioned R₁₁ may have. Preferable examplesof the substituent that X may have, include an alkyl group, an alkenylgroup, an aryl group, a heterocyclic group, a halogen atom, an alkoxygroup, an aryloxy group, an alkylthio group, an arylthio group, a cyanogroup, an acylamino group, an alkyl- and aryl-sulfonylamino group, analkoxy carboxyl group, a carbamoyl group, a sulfamoyl group, analkylamino group and an arylamino group.

Preferably the carbon atom adjacent to the position of the amido groupon the aryl group, bonds with a halogen atom (e.g., fluorine, chlorine),an alkyl group (e.g., methyl), an alkoxy group (e.g., methoxy,isopropyloxy, dodecyloxy), or an aryloxy group (e.g., phenyloxy). Amongthese groups, a halogen atom and an alkoxy group are more preferred. Analkoxy group is furthermore preferred.

In the coupler of the present invention, X is preferably a phenyl group.Assuming that the position where the phenyl group bonds with the amidogroup is the 1-position, the phenyl group preferably has theabove-mentioned substituent at least at the 2-position, more preferablyhas the substituents at the 2- and 5-positions.

In formula (IA), Y represents a hydrogen atom, or a group that iscapable of being split-off upon a coupling reaction with an oxidizedproduct of a developing agent. Examples of Y include a group that splitsoff with a nitrogen, oxygen, or sulfur atom (a splitting-off atom) and ahalogen atom (e.g., chlorine, bromine).

Examples of the group that splits off with a nitrogen atom, include aheterocyclic group (preferably a 5- to 7-membered substituted orunsubstituted, saturated or unsaturated, aromatic (herein the term“aromatic” is used to embrace a substance that has (4n+2) cyclicconjugated electrons) or non-aromatic, monocyclic or condensedheterocyclic groups, more preferably a 5- to 6-membered heterocyclicgroup, in which the ring-forming atom is selected from carbon, nitrogenand sulfur atoms and in addition at least one of hetero atoms selectedfrom nitrogen, oxygen and sulfur atoms is incorporated, with specificexamples of the heterocyclic ring including succinimide, maleinimide,phthalimide, diglycolimide, pyrrole, pyrazole, imidazole,1,2,4-triazole, tetrazole, indole, benzopyrazole, benzimidazole,benzotriazole, imidazoline-2,4-dione, oxazolidine-2,4-dionethiazolidine-2-one, benzimidazoline-2-one, benzoxazoline-2-one,benzothiazoline-2-one, 2-pyrroline-5-one, 2-imidazoline-5-one,indoline-2,3-dione, 2,6-dioxypurine parabanic acid,1,2,4-triazolidine-3,5-dione, 2-pyridone, 4-pyridone, 2-pyrimidone,6-pyridazone, 2-pyrazone, 2-amino-1,3,4-thiazolidine-4-one), acarbonamido group (e.g., acetamido, trifluoroacetamido), a sulfonamidogroup (e.g., methanesulfonamido, benzenesulfonamido), an arylazo group(e.g., phenylazo, naphthylazo), and a carbamoylamino group (e.g.,N-methyl carbamoylamino).

Preferred of the group that splits off with a nitrogen atom areheterocyclic groups, more preferably aromatic heterocyclic groups having1, 2, or 4 ring-forming nitrogen atom(s), or heterocyclic groupsrepresented by the following formula (LA). The heterocyclic groupsrepresented by the following formula (LA) are furthermore preferred.

In the formula (LA), L represents a residue that forms, together with—NC(═O)—, a 5- to 6-membered nitrogen-containing heterocyclic ring.

Examples of the residues are enumerated in the explanation of theabove-mentioned heterocyclic group, and such residues as enumeratedabove are more preferred.

Particularly preferably L is a residue that forms a 5-memberednitrogen-containing heterocyclic ring.

Examples of the group that splits off with an oxygen atom include anaryloxy group (e.g., phenoxy, 1-naphthoxy), a heterocyclic oxy group(e.g., pyridyloxy, pyrazolyloxy), an acyloxy group (e.g., acetoxy,benzoyloxy), an alkoxy group (e.g., methoxy, dodecyloxy), a carbamoyloxygroup (e.g., N,N-diethylcarbamoyloxy, morpholinocarbamoyloxy), anaryloxycarbonyloxy group (e.g., phenoxycarbonyloxy), analkoxycarbonyloxy group (e.g., methoxycarbonyloxy, ethoxycarbonyloxy),an alkylsulfonyloxy group (e.g., methanesulfonyloxy), and anarylsulfonyloxy group (e.g., benzenesulfonyloxy, toluenesulfonyloxy).

Preferred of these groups are an aryloxy group, an acyloxy group and aheterocyclic oxy group.

Examples of the group that splits off with a sulfur atom include anarylthio group (e.g., phenylthio, naphthylthio), a heterocyclic thiogroup (e.g., tetrazolylthio, 1,3,4-thiadiazolylthio, 1,3,4-oxazolylthio,benzimidazolylthio), an alkylthio group (e.g., methylthio, octylthio,hexadecylthio), an alkylsulfinyl group (e.g., methane sulfinyl), anarylsulfinyl group (e.g., benzenesulfinyl), an arylsulfonyl group (e.g.,benzenesulfonyl), and an alkylsulfonyl group (e.g., methanesulfonyl).

Preferred of the group that splits off with a sulfur atom are anarylthio group and a heterocyclic thio group. A heterocyclic thio groupis more preferred.

Y may be substituted with a substituent. Examples of the substituentinclude those enumerated as the substituent, which the above-mentionedR₁₁ may have.

Y is preferably the group that splits off with a nitrogen, oxygen, orsulfur atom, more preferably the group that splits off with a nitrogenatom. Further, those as enumerated as the preferable examples of thegroup that splits off with a nitrogen atom are preferred in the sameorder as mentioned above. Preferable examples of Y are further explainedbelow. Y is preferably an aromatic heterocyclic group having 1, 2, or 4ring-forming nitrogen atom(s), or a heterocyclic ring group representedby the above-mentioned formula (LA) (the latter is particularlypreferred), a group that splits off with an oxygen atom (particularlypreferably aryloxy, acyloxy, heterocyclic oxy) and a group that splitsoff with a sulfur atom (preferably arylthio, heterocyclic thio, andparticilarly preferably heterocyclic thio).

Y may be a photographically useful group. As the photographically usefulgroup, a development inhibitor, a desilvering accelerator, a redoxcompound, a dye, a coupler and the like, or their precursors areenumerated. Y is more preferably a development inhibitor or a precursorthereof. Examples of the development inhibitor or the precursor thereofinclude those as enumerated in JP-A-2000-17195. Preferable examples arethe same as described therein.

In order to render the coupler inmobile in a light-sensitive material,at least one of Q, R₁₁, X and Y has preferably 8 to 50 carbon atoms,more preferably 10 to 40 carbon atoms in total respectively, includingcarbon atoms of substituent(s) that they may have.

Preferable specific examples of the coupler represented by formula (IA)according to the present invention are shown below. However, the presentinvention should not be construed as being limited to these compounds.The present invention includes tautomers having a hydrogen atom moved ona carbonyl group or a nitrogen-containing 6-membered ring.

When any one of the exemplified compounds (which may also be referred toas dye-forming couplers) shown above is referred to in the followingdescription, a number X put in parentheses, that is, (X) attached to theexemplified compound is used to express the compound as “the coupler(X)”.

The following will describe specific synthetic examples of the compoundsrepresented by formula (IA).

SYNTHETIC EXAMPLE 1 Synthesis of the Coupler (10)

The coupler (10) was synthesized according to the following route:

27.9 g of isatoic acid anhydride was added to a mixed solution of 200 mlof an acetonitrile containing 53.8 g of aniline and 200 ml ofdimethylformamide, and the mixture was stirred at room temperature for 1hour. The resulting mixture was heated up to 80° C. and further stirredfor 1 hour. Thereafter, ethyl acetate and water were added to separatean organic layer from an aqueous layer. The organic layer was washedwith 1-normal aqueous solution of hydrochloric acid, 1-normal aqueoussolution of potassium carbonate and saturated brine, and then dried withmagnesium sulfate anhydride. Thereafter the solvent was removed byvacuum distillation. Crystallization from a mixed solvent of ethylacetate and hexane gave 20.1 g of Compound (A-1).

100 ml of an isopropyl alcohol solution containing 10.6 g of Compound(A-1) and 11.7 g of hydrochloride of iminoether was stirred for 3.5hours with heating under reflux. 11.7 g of hydrochloride of iminoetherwas added and further stirred with heating under reflux for 3.5 hours.Crystals precipitated by cooling with ice. Suction filtration gave 11.2g of Compound (A-2).

10 ml of a xylene solution containing 6.2 g of Compound (A-2) and 6.8 gof 2-chloro-5-dodecyloxycarbonylaniline was stirred for 4 hours withheating under reflux. Further, 1.2 g of Compound (A-2) was added andstirred for 5 hours with heating under reflux. Ethyl acetate and waterwere added to separate an organic layer from an aqueous layer. Theorganic layer was washed with 1-normal aqueous solution of hydrochloricacid and saturated brine, and then dried with magnesium sulfateanhydride. The solvent was removed by vacuum distillation.Crystallization from a mixed solvent of ethyl acetate and hexane gave6.0 g of Coupler (10).

SYNTHETIC EXAMPLE 2 Synthesis of the Coupler (1)

The coupler (1) was synthesized according to the following route:

To 70 ml of a methylenechloride solution containing 5.4 g of Coupler(10), 15 ml of a methylenechloride solution containing 0.48 ml ofbromine was added drop-wise under cooling with ice. After the mixturewas stirred at room temperature for 30 minutes, methylene chloride andwater were added to separate an organic layer from an aqueous layer. Theorganic layer was washed with saturated brine, and then dried withmagnesium sulfate anhydride. The solvent was removed by vacuumdistillation, to obtain a crude product of Compound (A-3).

To a solution which was prepared by dissolving 3.5 g of5,5-dimethyloxazolidine-2,4-dione and 3.8 ml of triethylamine in 50 mlof N,N-dimethyl acetoamide, a solution containing all the previouslysynthesized crude product of Compound (A-3) dissolved in 50 ml ofN,N-dimethylacetoamide was added drop-wise over 10 minutes at roomtemperature, and then stirred for 1 hour at room temperature. Ethylacetate and water were added to separate an organic layer from anaqueous layer. The organic layer was washed with 1-normal aqueoussolution of potassium carbonate, 1-normal aqueous solution ofhydrochloric acid and saturated brine, and then dried with magnesiumsulfate anhydride. The solvent was removed by vacuum distillation.Purification of the residue by silica gel column chromatography using amixed solvent of ethyl acetate and hexane as the eluate gave 3.7 g ofCoupler (1) as an amorphous product.Synthetic Example 3: Synthesis of the coupler (11) The coupler (11) wassynthesized according to the following route:

100 ml of a xylene solution containing 6.2 g of Compound (A-2) and 6.5 gof 2-methoxy-5-tetradecyloxycarbonylaniline was stirred with heating inreflux for 2 hours. Further, 0.5 g of p-toluenesulfonic acid monohydratewas added to the mixture, and the mixture was stirred with heating underreflux for 4 hours. Ethyl acetate and water were added to separate anorganic layer from an aqueous layer. The organic layer was washed with1-normal aqueous solution of hydrochloric acid and saturated brine, andthen dried with magnesium sulfate anhydride. The solvent was removed byvacuum distillation. Crystallization from a mixed solvent of ethylacetate and hexane gave 7.7 g of Coupler (11).

SYNTHETIC EXAMPLE 4 Synthesis of the Coupler (2)

The coupler (2) was synthesized according to the following route:

To 120 ml of a methylenechloride solution containing 6.9 g of Coupler(11), 20 ml of a methylenechloride solution containing 0.56 ml ofbromine was added drop-wise under cooling with ice. After the mixturewas stirred at room temperature for 30 minutes, methylene chloride andwater were added to separate an organic layer from an aqueous layer. Theorganic layer was washed with saturated brine, and then dried withmagnesium sulfate anhydride. The solvent was removed by vacuumdistillation, to obtain a crude product of Compound (A-4).

To a solution which was prepared by dissolving 4.3 g of5,5-dimethyloxazolidine-2,4-dione and 4.6 ml of triethylamine in 50 mlof N,N-dimethylacetoamide, a solution containing all the previouslysynthesized crude product of Compound (A-4) dissolved in 50 ml ofN,N-dimethylacetoamide was added drop-wise over 10 minutes at roomtemperature, and then stirred for 1 hour at room temperature. Ethylacetate and water were added to separate an organic layer from anaqueous layer. The organic layer was washed with 1-normal aqueoussolution of potassium carbonate, 1-normal aqueous solution ofhydrochloric acid and saturated brine, and then dried with magnesiumsulfate anhydride. The solvent was removed by vacuum distillation. Theresidue was purified by silica gel column chromatography using a mixedsolvent of ethyl acetate and hexane as the eluate. Crystallization frommethanol gave 4.4 g of Coupler (2).

Next, the compounds represented by formula (IB) among the compoundsrepresented by the aforementioned formula (I) of the present inventionare explained in detail.

The compound represented by formula (IB) of the present invention ischaracterized in the nitrogen-containing heterocyclic ring of anitrogen-containing heterocyclic acetoanilide compound. The aboveDescribed problems in the conventional technique have been solved, byintroducing a bulky substituent onto a nitrogen ring that constitutesthe above-said heterocyclic ring. It is assumed that the introduction ofthe bulky group has an influence on a dye structure control. If thedegree of bulkiness of the group is too large, satisfactory photographicproperties tends to become difficult to obtain, whereas if the degree istoo small, it is difficult to solve the above-descried problems in theconventional technique.

In formula (IB), R₁ represents a methylene group (—CH₂—), a methinegroup (—CH(−)—), or a carbon atom (—C(−)(−)—).

r represents an integer of 1 to 30. R₁s may be the same or differentindependently, when r is 2 or more. r preferably represents an integerof 1 to 10, more preferably 1 to 7, furthermore preferably 1 to 6, andmost preferably 1 to 3.

R₄ represents a substituent excepting a hydrogen atom. Examples of thesubstituent include halogen atoms, alkyl (including cycloalkyl andbicycloalkyl), alkenyl (including cycloalkenyl and bicycloalkenyl),alkynyl, aryl, heterocyclic, cyano, hydroxyl, nitro, carboxyl, alkoxy,aryloxy, silyloxy, heterocyclic oxy, acyloxy, carbamoyloxy,alkoxycarbonyloxy, aryloxycarbonyloxy, amino (including alkylamino andanilino), acylamino, aminocarbonylamino, alkoxycarbonylamino,aryloxycarbonylamino, sulfamoylamino, alkyl- or aryl-sulfonylamino,mercapto, alkylthio, arylthio, heterocyclic thio, sulfamoyl, sulfo,alkyl- or aryl-sulfinyl, alkyl- or aryl-sulfonyl, acyl, aryloxycarbonyl,alkoxycarbonyl, carbamoyl, aryl- or heterocyclic-azo, imido, phosphio,phosphinyl, phosphinyloxy, phosphinylamino, and silyl groups.

m represents an integer of 1 to 30. m preferably represents an integerof 1 to 6, more preferably 1 or more and 3 or less, and furthermorepreferably 1.

The above-mentioned substituents may be further substituted with asubstituent such as those described above.

Examples of the group of R₄ are further explained below.

Examples of these substituents include a halogen atom (e.g., chlorine,bromine, iodine); an alkyl group (preferably a straight-chain orbranched-chain, substituted or unsubstituted alkyl group, morepreferably the alkyl group having 1 to 30 carbon atoms, e.g., methyl,ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl,2-cyanoethyl, 2-ethylhexyl); a cycloalkyl group (preferably asubstituted or unsubstituted monocyclic cycloalkyl group having 3 to 30carbon atoms, e.g., cyclohexyl, cyclopentyl, and 4-n-dodecylcyclohexyl,and a polycycloalkyl group including groups composed of a polycyclicstructure such as a bicycloalkyl group (preferably a substituted orunsubstituted bicycloalkyl group having 5 to 30 carbon atoms, e.g.,bicyclo[1,2,2]heptane-2-yl and bicyclo[2,2,2]octane-3-yl) or atricycloalkyl group; more preferably a monocycloalkyl group or abicycloalkyl group and particularly preferably a monocyclic cycloalkylgroup); an alkenyl group (preferably a straight-chain or branched-chain,and substituted or unsubstituted alkenyl group, more preferably thealkenyl group having 2 to 30 carbon atoms, e.g., vinyl, allyl, prenyl,geranyl, oleyl); a cycloalkenyl group (preferably a substituted orunsubstituted cycloalkenyl group having 3 to 30 carbon atoms, e.g.,2-cyclopentene-1-yl, and 2-cyclohexene-1-yl; and a polycycloalkenylgroup such as a bicycloalkenyl group (preferably a substituted orunsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, e.g.,bicyclo[2,2,1]hepto-2-ene-1-yl or bicyclo[2,2,2]octo-2-ene-4-yl), or atricycloalkenyl group, with a monocyclic cycloalkenyl group beingparticularly preferred); an alkynyl group (preferably a substituted orunsubstituted alkynyl group having 2 to 30 carbon atoms, e.g., ethynyl,propargyl, trimethylsilylethynyl); an aryl group (preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms,e.g., phenyl, p-tolyl, naphthyl, m-chlorophenyl,o-hexadecanoylaminophenyl); a heterocyclic group (preferably 5- to7-membered substituted or unsubstituted, saturated or unsaturated,aromatic or non-aromatic, and monocyclic or condensed heterocyclicgroup, more preferably a heterocyclic group having ring-constitutingatoms selected from carbon, nitrogen and sulfur atoms, the heterocyclicgroup containing at least one hetero atom selected from the groupconsisting of nitrogen, oxygen and sulfur atoms; furthermore preferablya 5- to 6-membered aromatic heterocyclic group having 3 to 30 carbonatoms, e.g., 2-furyl, 2-thienyl, 2-pyridyl, 4-pyridyl, 2-pyrimidinyl,2-benzothiazolyl); a cyano group; a hydroxyl group; a nitro group; acarboxyl group; an alkoxy group (preferably a substituted orunsubstituted alkoxyl group having 1 to 30 carbon atoms, e.g., methoxy,ethoxy, isopropoxy, t-butoxy, n-octyloxy, 2-methoxyethoxy); an aryloxygroup (preferably a substituted or unsubstituted aryloxy group having 6to 30 carbon atoms, e.g., phenoxy, 2-methylphenoxy,2,4-di-t-amylphenoxy, 4-t-buthylphenoxy, 3-nitrophenoxy,2-tetradecanoylaminophenoxy); a silyloxy group (preferably a silyloxygroup having 3 to 20 carbon atoms, e.g., trimethylsilyloxy,t-butyldimethylsilyloxy); a herocyclic oxy group (preferably asubstituted or unsubstituted heterocyclic oxy group having 2 to 30carbon atoms, more preferably those having the heterocyclic moiety asdescribed to explain the above-mentioned heterocyclic group, e.g.,1-phenyltetrazole-5-oxy, 2-tetrahydropyranyloxy); an acyloxy group(preferably formyloxy, a substituted or unsubstituted alkylcarbonyloxygroup having 2 to 30 carbon atoms or a substituted or unsubstitutedarylcarbonyloxy group having 6 to 30 carbon atoms, e.g., formyloxy,acetyloxy, pivaloyloxy, stealoyloxy, benzoyloxy,p-methoxyphenylcarbonyloxy); a carbamoyloxy group (preferably asubstituted or unsubstituted carbamoyloxy group having 1 to 30 carbonatoms, e.g., N,N-dimethylcarbamoyloxy, N,N-diethylcarbamoyloxy,morpholinocarbonyloxy, N,N-di-n-octylaminocarbonyloxy,N-n-octylcarbamoyloxy); an alkoxycarbonyloxy group (preferably asubstituted or unsubstituted alkoxycarbonyloxy group having 2 to 30carbon atoms, e.g., methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, n-octylcarbonyloxy); an aryloxycarbonyloxy group(preferably a substituted or unsubstituted aryloxycarbonyloxy grouphaving 7 to 30 carbon atoms, e.g., phenoxycarbonyloxy,p-methoxyphenoxycarbonyloxy, p-n-hexadecyloxyphenoxycarbonyloxy); anamino group (preferably an unsubstituted amino group, a substituted orunsubstituted alkylamino group having 1 to 30 carbon atoms, asubstituted or unsubstituted arylamino group having 6 to 30 carbon atomsand a heterocyclic amino group having 0 (zero) to 30 carbon atoms e.g.,amino, methylamino, dimethylamino, anilino, N-methylanilino,diphenylamino, N-1,3,5-triazine-2-il amino); an acylamino group(preferably a formylamino group, a substituted or unsubstitutedalkylcarbonylamino group having 1 to 30 carbon atoms, and a substitutedor unsubstituted arylcarbonylamino group having 6 to 30 carbon atoms,e.g., formylamino, acetylamino, pivaloylamino, lauroylamino,benzoylamino and 3,4,5-tri-n-octyloxyphenylcarbonylamino); anaminocarbonylamino group (preferably a substituted or unsubstitutedaminocarbonylamino group having 1 to 30 carbon atoms, e.g.,carbamoylamino, N,N-dimethylaminocarbonylamino,N,N-diethylaminocarbonylamino, morpholinocarbonylamino); analkoxycarbonylamino group (preferably a substituted or unsubstitutedalkoxycarbonylamino group having 2 to 30 carbon atoms, e.g.,methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino,n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino); anaryloxycarbonylamino group (preferably a substituted or unsubstitutedaryloxycarbonylamino group having 7 to 30 carbon atoms, e.g.,phenoxycarbonylamino, p-chlorophenoxycarbonylamino,m-n-octyloxyphenoxycarbonyl amino); a sulfamoyl amino group (preferablya substituted or unsubstituted sulfamoylamino group having 0 (zero) to30 carbon atoms, e.g., sulfamoylamino, N,N-dimethylaminosulfonylamino,N-n-octyl aminosulfonylamino); an alkyl- or aryl-sulfonylamino group(preferably a substituted or unsubstituted alkyl sulfonylamino grouphaving 1 to 30 carbon atoms and a substituted or unsubstitutedarylsulfonylamino group having 6 to 30 carbon atoms, e.g.,methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino,2,3,5-trichlorophenylsulfonylamino, p-methylphenylsulfonylamino); amercapto group; an alkylthio group (preferably a substituted orunsubstituted alkylthio group having 1 to 30 carbon atoms, e.g.,methylthio, ethylthio, n-hexadecylthio); an arylthio group (preferably asubstituted or unsubstituted arylthio group having 6 to 30 carbon atoms,e.g., phenylthio, p-chlorophenylthio, m-methoxyphenylthio); aheterocyclic thio group (preferably a substituted or unsubstitutedheterocyclic thio group having 2 to 30 carbon atoms in which theheterocyclic moiety is preferably the same as that of theabove-described heterocyclic group, e.g., 2-benzothiazolylthio,1-phenyltetrazol-5-ylthio); a sulfamoyl group (preferably a substitutedor unsubstituted sulfamoyl group having 0 (zero) to 30 carbon atoms,e.g., N-ethylsulfamoyl, N-(3-dodecyloxypropyl)sulfamoyl, N,N-dimethylsulfamoyl, N-acetylsulfamoyl, N-benzoylsulfamoyl, N-(N′-phenylcarbamoyl)sulfamoyl); a sulfo group; an alkyl- or aryl-sulfinyl group (preferablya substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbonatoms or a substituted or unsubstituted arylsulfinyl group having 6 to30 carbon atoms, e.g., methylsulfinyl, ethylsulfinyl, phenylsulfinyl,p-methylphenylsulfinyl); an alkyl- or aryl-sulfonyl group (preferably asubstituted or unsubstituted alkylsulfonyl group having 1 to 30 carbonatoms and a substituted or unsubstituted arylsulfonyl group having 6 to30 carbon atoms, e.g., methylsulfonyl, ethylsulfonyl, phenylsulfonyl,p-methylphenylsulfonyl); an acyl group (preferably a formyl group, asubstituted or unsubstituted alkylcarbonyl group having 2 to 30 carbonatoms and a substituted or unsubstituted arylcarbonyl group having 7 to30 carbon atoms, e.g., acetyl, pivaloyl, 2-chloroacetyl, stearoyl,benzoyl, p-n-octyloxyphenylcarbonyl); an aryloxycarbonyl group(preferably a substituted or unsubstituted aryloxycarbonyl group having7 to 30 carbon atoms, e.g., phenoxycarbonyl, o-chlorophenoxycarbonyl,m-nitrophenoxycarbonyl, p-t-butylphenoxycarbonyl); an alkoxycarbonylgroup (preferably a substituted or unsubstituted alkoxycarbonyl grouphaving 2 to 30 carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl,t-butoxycarbonyl, n-octadecyloxycarbonyl); a carbamoyl group (preferablya substituted or unsubstituted carbamoyl group having 1 to 30 carbonatoms, e.g., carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl,N,N-di-n-octylcarbamoyl, N-(methylsulfonyl)carbamoyl); an aryl- orheterocyclic-azo group (preferably a substituted or unsubstituted arylazo group having 6 to 30 carbon atoms, and a substituted orunsubstituted heterocyclic azo group having 3 to 30 carbon atoms inwhich the heterocyclic moiety is preferably the same as that of theabove-described heterocyclic group, e.g., phenylazo, p-chlorophenylazo,5-ethylthio-1,3,4-thiadiazole-2-yl azo); an imido group (preferably asubstituted or unsubstituted imido group having 2 to 30 carbon atoms,e.g., N-succinimido, N-phthalimido); a phosphino group (preferably asubstituted or unsubstituted phosphino group having 2 to 30 carbonatoms, e.g., dimethylphosphino, diphenylphosphino,methylphenoxyphosphino); a phosphinyl group (preferably a substituted orunsubstituted phosphinyl group having 2 to 30 carbon atoms, e.g.,phosphinyl, dioctyloxyphosphinyl, diethoxyphosphinyl); a phosphinyloxygroup (preferably a substituted or unsubstituted phosphinyloxy grouphaving 2 to 30 carbon atoms, e.g., diphenoxyphosphinyloxy,dioctyloxyphosphinyloxy); a phosphinylamino group (preferably asubstituted or unsubstituted phosphinylamino group having 2 to 30 carbonatoms, e.g., dimethoxyphosphinylamino, dimethylaminophosphinylamino);and a silyl group (preferably a substituted or unsubstituted silyl grouphaving 3 to 30 carbon atoms, e.g., trimethylsilyl, t-butyldimethylsilyl,phenyldimethylsilyl).

Among the group represented by R₄, a hydrogen atom(s) in thesubstituents may be replaced with the above-described group. Examples ofthese group R₄s include an alkylcarbonylaminosulfonyl group, anarylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group,and an arylsulfonyl aminocarbonyl group. As the specific examples, amethylsulfonyl aminocarbonyl, a p-methylphenylsulfonylaminocarbonyl, anacetylaminosulfonyl, a benzoylaminosulfonyl, adodecylcarbonylaminosulfonyl, a p-chlorophenylcarbonylaminosulfonyl, adodecanesulfonylaminocarbonyl, a p-toluene sulfonylaminocarbonyl, or ap-dodecyloxybenzenesulfonylaminocarbonyl group are enumerated.

The groups represented by R₄ may be the same or different independently,or the group represented by R₄ may bond with each other to form a ring,preferably a 5-to 7-membered saturated or unsaturated ring, when m is 2or more. The ring may be an alicyclic ring, an aromatic ring, or aheterocyclic ring. Examples of these rings include a benzene, a furan, athiophene, a cyclopentene or a cyclohexane ring.

The rings that are formed by bonding of these substituents with eachother, may have a substituent such as those enumerated as the grouprepresented by the above-mentioned R₄.

Further, R₄s may combine with each other to form a multiple bond.Specifically, the —(R₁)_(r)—(R₄)_(m) group may be an alkenyl group or analkynyl group. However, the —(R₁)_(r)—(R₄)_(m) group does not representa straight-chain alkyl group.

At least one R₄, preferably all the R₄s, preferably bonds with a carbonatom(s) at the α-, β-, γ- and/or δ-position(s) in the (R₁)_(r). Herein,the position of a carbon atom in (R₁)_(r) that directly bonds with thenitrogen atom on the heterocyclic ring composed of Q and the—N—C=N-moiety, is referred to as “α-position”. Likewise, the position ofa carbon atom adjacent to the α-position carbon atom is referred to as“β-position”, the further adjacent position thereto as “y-position”, andthe still further adjacent position thereto as “β-position”, in turn.Further, more preferably, in case where R₄ exclusively consists of alkylgroups, at least one of the alkyl groups preferably bonds with a carbonatom at the α-position or β-position. Besides, more preferably in casewhere at least one of R₄S is an aryl group, at least one of the arylgroup(s) preferably bonds with a carbon atom at the α-position orβ-position. On the other hand, in case where R₄ is a substituent whichneither contains an aryl group nor exclusively consists of alkyl groups,the R₄ more preferably bonds with a carbon atom at the β-position,γ-position or δ-position (further preferably β- or γ-position).

In case where r is in the range of 8 to 30, bond of the substituents ofR₄ is not limited to the particular position, but the above-describedpositions are preferable. On the other hand, a preferable range of r isthe same as mentioned above.

The total carbon atoms of the substituent's of R₄ is preferably 2 to 50,more preferably 7 to 45, further preferably 10 to 40, and mostpreferably 15 to 40.

Preferred of these substituents of R₄ are an alkyl group, an alkenylgroup, an aryl group, a heterocyclic group, a halogen atom, an aminogroup, a hydroxyl group, a carboxyl group, a sulfo group, an acylaminogroup, an alkyl- or aryl-sulfonylamino group, a carbamoyl group, asulfamoyl group, an acyl group, a sulfonyl group, an alkoxycarbonylgroup, an aryloxycarbonyl group, an alkylthio group, an arylthio group,a cyano group, an alkoxy group and an aryloxy group.

More preferred of these substituents of R₄ are an alkyl group, an arylgroup, a heterocyclic group, a halogen atom, an amino group, a carboxylgroup, a sulfo group, an acylamino group, an alkyl- oraryl-sulfonylamino group, a carbamoyl group, a sulfamoyl group, an acylgroup, a sulfonyl group, an alkoxycarbonyl group, an aryloxycarbonylgroup, an alkylthio group, an arylthio group, a cyano group, an alkoxygroup and an aryloxy group. An aryl group, an alkoxy group and anaryloxy group are furthermore preferred.

Concentrating on the —(R₁)_(r)—(R₄)_(m) group of the dye-forming couplerrepresented by formula (IB) according to the present invention, theabove-mentioned preferable group of R₄ can be grouped into thefollowings:

Group 1

In case where the —(R₁)_(r)—(R₄)_(m) group is an unsubstituted branchedalkyl group:

The total carbon atoms of the (R₁)_(r) and (R₄)_(m) is preferably 8 ormore, more preferably 8 to 40, and further preferably 10 to 30. R₄preferably bonds with (R₁)_(r) at the α-position or 13-position.

When R₄ bonds with (R₁)_(r) at the α-position, the bulkiness at theneighborhood of the resultant dye increases, even though the totalcarbon atoms of the above-mentioned group is 7 or less. Consequently,such embodiment is also preferable in the second place to the above.

Group 2

In case where at least one of R₄ is an alkoxy group or an aryloxy group:

The total carbon atoms of the alkoxy group or the aryloxy group ispreferably 8 or more, more preferably 8 to 40, and further preferably 10to 30. The alkoxy group or the aryloxy group preferably bonds with(R₁)_(r) at the β-position, γ-position or β-position (more preferably β-or γ-position).

Group 3

In case where at least one of R₄ is an aryl group, a heterocyclic group,a halogen atom, an amino group, a carboxyl group, a sulfo group, anacylamino group, an alkyl- or aryl-sulfonylamino group, a carbamoylgroup, a sulfamoyl group, an acyl group, a sulfonyl group, analkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, anarylthio group, or a cyano group:

When the at least one group R₄ is the aryl group, the aryl grouppreferably bonds with (R₁)_(r) at the α-position or β-position,particularly preferably α-position. On the other hand, when R₄ does notcontain an aryl group, at least one R₄ of a heterocyclic group, ahalogen atom, an amino group, a carboxyl group, a sulfo group, anacylamino group, an alkyl- or aryl-sulfonylamino group, a carbamoylgroup, a sulfamoyl group, an acyl group, a sulfonyl group, analkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, anarylthio group, and a cyano group preferably bonds with (R₁)_(r) at theβ-position or γ-position.

Among these groups, it is more preferable that at least one of R₄ is anaryl group. The (R₄)_(m) in which R₄ is an aryl group and m is 1, isfurthermore preferred. The —(R₁)_(r)—(R₄)_(m) group as a whole including—(R₁)_(r) is most preferably a benzyl group.

In formula (IB), Q represents a residue that forms, together with the—N—C═N— moiety, a nitrogen-containing 6-membered heterocyclic ring. Thenitrogen-containing heterocyclic ring is a substituted or unsubstitutedheterocyclic ring, more preferably a heterocyclic ring composed of acarbon atom and a nitrogen atom, as ring-forming atoms, and having 2 to4 nitrogen atoms; furthermore preferably a nitrogen-containing6-membered heterocyclic ring having 2 to 30 carbon atoms and 2 nitrogenatoms. Examples of the nitrogen-containing 6-membered ring that isformed by Q together with the —N—C═N— moiety, include 4-pyrimidone,1,3-diazine-4,6-dione, 1,3,5-triazine-2-one and 1,2,4-triazine-5-one.The nitrogen-containing 6-membered ring that is formed by Q togetherwith the —N—C═N— moiety, may have a substituent. Examples of thesubstituent are the same as those of R₄ mentioned above.

Further, the substituents adjacent to each other may combine together toform a ring, preferably a 5- to 7-membered saturated or unsaturatedring, and the ring may be alicyclic, aromatic or heterocyclic ring. Asthe examples of the ring, benzene, furan, thiophene, cyclopentane, andcyclohexane rings are enumerated.

Each of the above-mentioned substituents and the rings that are formedby combination of some of these substituents with each other, also mayhave a substituent. Examples of the substituent are the same as those ofR₄ mentioned above.

The total carbon atoms of the above-mentioned substituent is preferably2 to 50, more preferably 8 to 45, furthermore preferably 15 to 40.

Preferred of these substituents are an alkyl group, an alkenyl group, anaryl group, a heterocyclic group, a halogen atom, an alkoxy group, anaryloxy group, an alkylthio group, an arylthio group, a cyano group, anacylamino group, an alkyl- or aryl-sulfonylamino group, analkoxycarboxyl group, a carbamoyl group, a sulfamoyl group, analkylamino group and an arylamino group.

Q is preferably a residue that forms, together with the —N—C═N— moiety,a 4-pyrimidone ring. More preferably Q is represented by—C(—R₂)═C(—R₃)—CO—. R₂ and R₃, when combined with each other, form,together with the —C═C-moiety, a 5- to 7-membered ring, or R₂ and R₃each independently represent a hydrogen atom or a substituent. The ringthat is formed by combination of R₂ and R₃ together with the —C═C—moiety, is preferably a 5- to 7-membered alicyclic, aromatic orheterocyclic ring. As examples of the ring, benzene, pyrazole, furan,thiophene, cyclopentene and cyclohexene rings are enumerated. Morepreferably the ring is a 6-membered aromatic ring. A benzene ring ismost preferred.

When R₂ and R₃ each represent a substituent, R₂ and R₃ may be the sameor different independently. Examples of the substituent are the same asthose of R₄ mentioned above.

In formula (IB), X represents an aryl group. The aryl group ispreferably a substituted or unsubstituted aryl group having 6 to 30carbon atoms, such as a phenyl group and a naphthyl group. X may have asubstituent. Examples of the substituent are the same as those of R₄mentioned above. Preferable examples of the substituent that X may have,include an alkyl group, an alkenyl group, an aryl group, a heterocyclicgroup, a halogen atom, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, a cyano group, an acylamino group, an alkyl-or aryl-sulfonylamino group, an alkoxycarboxyl group, a carbamoyl group,a sulfamoyl group, an alkylamino group and an arylamino group.

Preferably the carbon atom adjacent to the position of the amido groupon the aryl group, bonds with a halogen atom (e.g., fluorine, chlorine),an alkyl group (e.g., methyl), an alkoxy group (e.g., methoxy,isopropyloxy, dodecyloxy), or an aryloxy group (e.g., phenyloxy). Amongthese groups, a halogen atom and an alkoxy group are more preferred. Analkoxy group is furthermore preferred.

In the coupler of the present invention, X is preferably a phenyl group.Assuming that the position where the phenyl group bonds with the amidogroup is the 1-position, the phenyl group preferably has theabove-mentioned substituent at least at the 2-position, more preferablyhas the substituents at the 2- and 5-positions.

In formula (IB), Y represents a hydrogen atom, or a group that iscapable of being split-off upon a coupling reaction with an oxidizedproduct of a developing agent. Examples of Y include a group that splitsoff with a nitrogen, oxygen, or sulfur atom (a splitting-off atom) and ahalogen atom (e.g., chlorine, bromine).

Examples of the group that splits off with a nitrogen atom, include aheterocyclic group (preferably a 5- to 7-membered substituted orunsubstituted, saturated or unsaturated, aromatic (herein the term“aromatic” is used to embrace a substance that has (4n+2) cyclicconjugated electrons) or non-aromatic, monocyclic or condensedheterocyclic group, more preferably a 5- to 6-membered heterocyclicgroup, in which the ring-forming atom is selected from carbon, nitrogenand sulfur atoms and in addition at least one of hetero atoms selectedfrom nitrogen, oxygen and sulfur atoms is incorporated, with specificexamples of the heterocyclic ring including succinimide, maleinimide,phthalimide, diglycolimide, pyrrole, pyrazole, imidazole,1,2,4-triazole, tetrazole, indole, benzopyrazole, benzimidazole,benzotriazole, imidazoline-2,4-dione, oxazolidine-2,4-dione,thiazolidine-2-one, benzimidazoline-2-one, benzoxazoline-2-one,benzothiazoline-2-one, 2-pyrroline-5-one, 2-imidazoline-5-one,indoline-2,3-dione, 2,6-dioxypurine parabanic acid,1,2,4-triazolidine-3,5-dione, 2-pyridone, 4-pyridone, 2-pyrimidone,6-pyridazone, 2-pyrazone, 2-amino-1,3,4-thiazolidine-4-one), acarbonamido group (e.g., acetamido, trifluoroacetamido), a sulfonamidogroup (e.g., methanesulfonamido, benzenesulfonamido), an arylazo group(e.g., phenylazo, naphthylazo), and a carbamoylamino group (e.g.,N-methyl carbamoylamino).

Preferred of the group that splits off with a nitrogen atom is aheterocyclic group, more preferably an aromatic heterocyclic grouphaving 1, 2, or 4 ring-forming nitrogen atoms, or a heterocyclic grouprepresented by the following formula (LB). The heterocyclic grouprepresented by the following formula (LB) are furthermore preferred.

In the formula (LB), L represents a residue that forms, together with—NC(═O)—, a 5- to 6-membered nitrogen-containing heterocyclic ring.

Examples of the residues are enumerated in the explanation of theabove-mentioned heterocyclic group, and such residues as enumeratedabove are more preferred.

Particularly preferably L is a residue that forms, together with the—NC(═O)—, a 5-membered nitrogen-containing heterocyclic ring.

Examples of the group that splits off with an oxygen atom include anaryloxy group (e.g., phenoxy, 1-naphthoxy), a heterocyclic oxy group(e.g., pyridyloxy, pyrazolyloxy), an acyloxy group (e.g., acetoxy,benzoyloxy), an alkoxy group (e.g., methoxy, dodecyloxy), a carbamoyloxygroup (e.g., N,N-diethylcarbamoyloxy, morpholinocarbamoyloxy), anaryloxycarbonyloxy group (e.g., phenoxycarbonyloxy), analkoxycarbonyloxy group (e.g., methoxycarbonyloxy, ethoxycarbonyloxy),an alkylsulfonyloxy group (e.g., methanesulfonyloxy), and anarylsulfonyloxy group (e.g., benzenesulfonyloxy, toluenesulfonyloxy).

Preferred of these groups are an aryloxy group, an acyloxy group and aheterocyclic oxy group.

Examples of the group that splits off with a sulfur atom include anarylthio group (e.g., phenylthio, naphthylthio), a heterocyclic thiogroup (e.g., tetrazolylthio, 1,3,4-thiadiazolylthio, 1,3,4-oxazolylthio,benzimidazolylthio), an alkylthio group (e.g., Methylthio, octylthio,hexadecylthio), an alkylsulfinyl group (e.g., methanesulfinyl), anarylsulfinyl group (e.g., benzenesulfinyl), an arylsulfonyl group (e.g.,benzenesulfonyl), and an alkylsulfonyl group (e.g., methanesulfonyl).

Preferred of the group that splits off with a sulfur atom are anarylthio group and a heterocyclic thio group. A heterocyclic thio groupis more preferred.

Y may be substituted with a substituent. Examples of the substituentinclude those enumerated as the substituent of R₄ described above.

Y is preferably the group that splits off with a nitrogen, an oxygen, ora sulfur atom, more preferably the group that splits off with a nitrogenatom. Further, those as enumerated as the preferable examples of thegroup that splits off with a nitrogen atom are more preferred in thesame order as Y. Preferable examples of Y are further explained below.

Y is preferably an aromatic heterocyclic group having 1, 2, or 4ring-forming nitrogen atom(s), or a heterocyclic group represented bythe above-mentioned formula (LB) (the latter is particularly preferred),a group that splits off with an oxygen atom (particularly preferablyaryloxy, acyloxy, heterocyclic oxy) and a group that splits off with asulfur atom (preferably arylthio, heterocyclic thio, and particilarlypreferably heterocyclic thio).

Preferably, Y may be a photographically useful group. As thephotographically useful group, a development inhibitor, a desilveringaccelerator, a redox compound, a dye, a coupler and the like, or theirprecursors are enumerated. Y is more preferably a development inhibitoror a precursor thereof. Examples of the development inhibitor or theprecursor thereof include those as enumerated in JP-A-2000-17195.Preferable examples are the same as described therein.

In order to render the coupler inmobile in a light-sensitive material,at least one of Q, R₁, R₄, X and Y has preferably 8 to 50 carbon atoms,more preferably 10 to 40 carbon atoms in total respectively, includingcarbon atoms of substituent(s) that they may have.

Preferable specific examples of the coupler represented by formula (IB)according to the present invention are shown below. However, the presentinvention should not be construed as being limited to these compounds.The present invention includes tautomers having a hydrogen atom moved ona carbonyl group or a nitrogen-containing 6-membered ring.

When any one of the exemplified compounds (which may also be referred toas dye-forming couplers) shown above is referred to in the followingdescription, a number X put in parentheses, that is, (X) attached to theexemplified compound is used to express the compound as “the coupler(X)”.

The following will describe specific synthetic examples of the compoundsrepresented by formula (IB).

SYNTHETIC EXAMPLE 2-1 Synthesis of the Coupler (10B)

The coupler (10B) was synthesized according to the following route:

32.2 g of benzylamine was added, drop-wise, with stirring, to 200 ml ofan acetonitrile solution containing 48.9 g of isatoic acid anhydride,and the resulting mixture was stirred. The resulting mixture was heatedup to 60° C. and further stirred for 10 minutes. Thereafter, ethylacetate and water were added thereto, to separate an organic layer froman aqueous layer. The organic layer was dried with magnesium sulfateanhydride, and then the solvent was removed by vacuum distillation.Crystallization from a mixed solvent of ether and hexane gave 54.6 goofCompound (A-1B).

200 ml of an ethyl alcohol solution containing 24.9 g of Compound(A-1B), 21.6 g of hydrochloride of iminoether and 10.5 g ofparatoluenesulfonic acid monohydrate was stirred for 3 hours withheating under reflux. After cooling, 21.6 g of hydrochloride ofiminoether was added and further stirred with heating under reflux for 1hour. Ethyl acetate and water were added to separate an organic layerfrom an aqueous layer. The organic layer was dried with magnesiumsulfate anhydride. The solvent was removed by vacuum distillation.Crystallization from a mixed solvent of ether and hexane gave 33.6 g ofCompound (A-2B).

50 ml of p-xylene solution containing 6.5 g of Compound (A-2B) and 6.5 gof 2-chloro-5-dodecyloxycarbonylaniline was stirred for 2 hours withheating under reflux. Further, 0.2 g of p-toluenesulfonic acidmonohydrate was added and stirred for 4 hours with heating under reflux.Ethyl acetate and water were added to separate an organic layer from anaqueous layer. The organic layer was washed with 1-normal aqueoussolution of hydrochloric acid and saturated brine, and then dried withmagnesium sulfate anhydride. The solvent was removed by vacuumdistillation. Crystallization from a mixed solvent of ethyl acetate andhexane gave 6.7 g of Coupler (10B).

SYNTHETIC EXAMPLE 2-2 Synthesis of the Coupler (1B)

The coupler (1B) was synthesized according to the following route:

To 70 ml of a methylene chloride solution containing 5.5 g of Coupler(10B), 15 ml of a methylene chloride solution containing 0.48 ml ofbromine was added drop-wise under cooling with ice. After the mixturewas stirred at room temperature for 30 minutes, methylene chloride andwater were added to separate an organic layer from an aqueous layer. Theorganic layer was washed with saturated brine, and then dried withmagnesium sulfate anhydride. The solvent was removed by vacuumdistillation to obtain a crude product of Compound (A-3B).

To a solution which was prepared by dissolving 3.5 g of 5,5-dimethyloxazolidine-2,4-dione and 3.8 ml of triethylamine in 50 ml ofN,N-dimethyl acetoamide, a solution containing all the previouslysynthesized crude product of Compound (A-3B) dissolved in 50 ml ofN,N-dimethyl acetoamide was added drop-wise over 10 minutes at roomtemperature, and then stirred for 1 hour at room temperature. Ethylacetate and water were added to separate an organic layer from anaqueous layer. The organic layer was washed with 1 normal aqueoussolution of potassium carbonate, 1 normal aqueous solution ofhydrochloric acid and saturated brine, and then dried with magnesiumsulfate anhydride. The solvent was removed by vacuum distillation.Purification of the residue by silica gel column chromatography using amixed solvent of ethyl acetate and hexane as the eluate gave 4.0 g ofCoupler (1B) as an amorphous product.

SYNTHETIC EXAMPLE 2-3 Synthesis of the Coupler (11B)

The coupler (11B) was synthesized according to the following route:

58.3 g of 3-(2,4-di-t-amyl-phenoxy)-propylamine was added with stirringto 200 ml of an acetonitrile solution containing 34.3 g of isatoic acidanhydride, and the resulting mixture was stirred. The resulting mixturewas heated up to 40° C. and further stirred for 15 minutes. Thereafter,ethyl acetate and water were added to separate an organic layer from anaqueous layer. The organic layer was dried with magnesium sulfateanhydride, and then the solvent was removed by vacuum distillation, toobtain 81.3 g of Compound (B-1B) as an oily product.

200 ml of an ethyl alcohol solution containing 41.1 g of Compound (B-1B)and 39.1 g of hydrochloride of iminoether was stirred at 30° C. for 1hour. 8.6 g of p-toluenesulfonic acid monohydrate was added and furtherstirred with heating under reflux for 2 hours. Ethyl acetate and waterwere added to separate an organic layer from an aqueous layer. Theorganic layer was dried with magnesium sulfate anhydride and then thesolvent was removed by vacuum distillation. Crystallization from amethanol solvent gave 31.8 g of Compound (B-2B).

20 ml of p-xylene solution containing 10.1 g of Compound (B-2B) and 3.9g of 2-methoxy-5-ethoxycarbonylaniline was stirred with heating underreflux for 4 hours. Ethyl acetate and water were added to separate anorganic layer from an aqueous layer. The organic layer was washed with1-normal aqueous solution of hydrochloric acid and saturated brine, andthen dried with magnesium sulfate anhydride. The solvent was removed byvacuum distillation. Crystallization from a mixed solvent of ethylacetate and hexane gave 6.3 g of Coupler (11B).

SYNTHETIC EXAMPLE 2-4 Synthesis of the Coupler (2B)

The coupler (2B) was synthesized according to the following route:

To 120 ml of a methylene chloride solution containing 5.9 g of Coupler(11B), 20 ml of a methylene chloride solution containing 0.56 ml ofbromine was added drop-wise under cooling with ice. After the mixturewas stirred at room temperature for 30 minutes, methylene chloride andwater were added to separate an organic layer from an aqueous layer. Theorganic layer was washed with saturated brine, and then dried withmagnesium sulfate anhydride. The solvent was removed by vacuumdistillation to obtain a crude product of Compound (B-3B).

To a solution which was prepared by dissolving 4.3 g of5,5-dimethyloxazolidine-2,4-dione and 4.6 ml of triethylamine in 50 mlof N,N-dimethyl acetoamide, a solution containing all the previouslysynthesized crude product of Compound (B-3B) dissolved in 50 ml ofN,N-dimethyl acetoamide was added drop-wise over 10 minutes at roomtemperature, and then stirred for 1 hour at room temperature. Ethylacetate and water were added to separate an organic layer from anaqueous layer. The organic layer was washed with 1 normal aqueoussolution of potassium carbonate, 1 normal aqueous solution ofhydrochloric acid and saturated brine, and then dried with magnesiumsulfate anhydride. The solvent was removed by vacuum distillation. Theresidue was purified by silica gel column chromatography using a mixedsolvent of ethyl acetate and hexane as the eluate. Crystallization frommethanol gave 4.1 g of Coupler (2B).

The dye-forming couplers of the present invention are explained above,referring to the formulae (IA) and (IB) as examples, and theseexplanations, as they are, can also be applied to the formula (I) thatincludes said formulae (IA) and (IB).

(Silver Halide Photographic Light-Sensitive Material)

The light-sensitive material of the present invention is a silver halidephotographic light-sensitive material, in which at least onelight-sensitive layer is formed on a support, and the light-sensitivematerial contains the dye-forming coupler that is the compoundrepresented by formula (I) of the present invention (for example, thecompound represented by formula (IA) or (IB); the same is appliedhereinafter), in at least one layer of the light-sensitive layer(s). Thecoupler is generally contained in a hydrophilic colloid layer composedof an ordinary gelatin binder. An ordinary light-sensitive material canbe made by providing light-sensitive emulsion layers (light-sensitivelayers) composed of at least one blue-sensitive silver halide emulsionlayer, at least one green-sensitive silver halide emulsion layer, and atleast one red-sensitive silver halide emulsion layer, on a support. Theorder of these light-sensitive layers may be selected arbitrarily. Aninfrared ray-sensitive silver halide emulsion layer may be used insteadof at least one of the above-mentioned light-sensitive emulsion layers.Color reproduction based on subtractive color processes can be performedby incorporating, into each of these light-sensitive emulsion layers, asilver halide emulsion having sensitivity in the correspondingwavelength range, and a coupler for forming a dye having a colorcomplementary to the color of sensitizing light. However, thelight-sensitive emulsion layer and the developed hue of the coupler maynot have a corresponding relationship as described above.

The dye-forming coupler represented by formula (I) can be incorporatedinto any one of the light-sensitive emulsion layers (preferably, theblue-sensitive silver halide emulsion layer or the green-sensitivesilver halide emulsion layer, particularly preferably the blue-sensitivesilver halide emulsion layer).

The dye-forming coupler represented by formula (I) is useful mainly as ayellow coupler or a magenta coupler, particularly as a yellow coupler,when combined with a p-phenylenediamine color-developing agent.Therefore, in the case that a p-phenylenediamine is used as acolor-developing agent for the silver halide photographiclight-sensitive material of the present invention, the dye-formingcoupler represented by formula (I) is incorporated preferably into theyellow coupler- or magenta coupler-containing color-forming layer,particularly preferably into the yellow color-forming layer. In systemswherein a color-developing agent other than p-phenylenediamines is used,the dye-forming coupler represented by formula (I) is useful as adye-forming coupler that can give a dye having various types of hue.

In the silver halide photographic light-sensitive material of thepresent invention, the coupler is added preferably in an amount of1×10⁻⁻³ to 1 mole, more preferably in an amount of 2×10⁻³ to 3×10⁻¹mole, per mole of silver halide.

The coupler of the present invention may be incorporated in alight-sensitive material by various known dispersion processes. It ispreferred to use an oil-in-water dispersion process in which first acompound is dissolved in a high-boiling-point organic solvent (incombination with a low-boiling-point organic solvent as occasiondemands), thereby forming a solution and then the resulting solution isemulsified and dispersed in an aqueous gelatin solution, which is thenadded to a silver halide emulsion. Examples of the high-boiling-pointorganic solvent for use in the oil-in-water dispersion process aredescribed in, for example, JP-A-5-313327, JP-A-5-323539, JP-A-5-323541,JP-A-6-258803, JP-A-8-262662, and U.S. Pat. No. 2,322,027. Further, thesteps, effects and specific examples of latex polymers for impregnation,which are used in the latex dispersion process as one of polymerdispersion process, are described in, for example, U.S. Pat. No.4,199,363, West German Patent Application (OLS) Nos. 2,541,274 and2,541,230, JP-B-53-41091 (“JP-B” means examined Japanese patentpublication), and European Patent Publication No. 029104. Further,dispersion processes using an organic solvent-soluble polymer aredescribed in, for example, PCT International Publication WO 88/00723 andJP-A-5-150420. Methacrylate-series or acrylamide-series polymers arepreferred. In particular, the use of acrylamide-series polymers ispreferred, in view of enhancing image-fastness.

The term “high boiling point” herein used refers to a boiling point of175° C. or more at ordinary pressure.

Examples of the high-boiling-point solvent for use in the presentinvention are described in, for example, U.S. Pat. No. 2,322,027.Specific examples of the high-boiling-point organic solvent having aboiling point of 175° C. or more at ordinary pressure include phthalicacid esters {e.g., dibutyl phthalate, dicyclohexyl phthalate,di-2-ethylhexyl phthalate, decyl phthalate, bis(2,4-di-tert-amylphenyl)phthalate, bis(2,4-di-tert-amylphenyl) iso-phthalate,bis(1,1-di-ethylpropyl) phthalate}, esters of phosphoric acid orphosphonic acid (e.g., triphenyl phosphate, tricresyl phosphate,2-ethylhexyldiphenyl phosphate, tricyclohexyl phosphate, tri-2-ethlhexylphosphate, tridodecyl phosphate, tributoxyethyl phosphate,trichloropropyl phosphate, di-2-ethylhexylphenyl phosphonate), benzoicacid esters (e.g., 2-ethylhexyl benzoate, dodecyl benzoate, 2-ethylhexylp-hydroxybenzoate), amides (e.g., N,N-diethyldodecaneamide,N,N-diethyllaurylamide, N-tetradecylpyrrolidone), sulfonamides (e.g.,N-butylbenzenesulfonamide), alcohols and phenols (e.g., isostearylalcohol, 2,4-di-tert-amylphenol), aliphatic carboxylic acid esters(e.g., bis-(2-ethylhexyl) sebacate, dioctyl azelate, glyceroltributylate, isostearyl lactate, trioctyl citrate), aniline derivatives(e.g., N,N-dibutyl-2-butory-5-tert-octylaniline), hydrocarbons (e.g.,paraffin, dodecylbenzene, diisopropylnaphthalene), and chlorinatedparaffins. In particular, the foregoing phosphoric acid esters, andhydrogen-providing compounds described in JP-A-6-258803 andJP-A-8-262662 are preferably used, since they help to provide anexcellent hue.

In order to reduce a load to environment, it is preferred to usecompounds described in European Patent Nos. EP-969320A1 and EP-969321A1,in place of the foregoing phthalic acid esters. In addition to theabove-mentioned compounds, tributyl citrate, pentaglycelol triesters andthe like may be used.

The dielectric constant of the high-boiling-point organic solvent variesdepending on the purpose for use, but it is preferably in the range of2.0 to 7.0, more preferably in the range of 3.0 to 6.0.

The high-boiling-point organic solvent is used preferably in an amountof 0 to 10 times of the mass of the coupler, more preferably in anamount of 0 to 4 times thereof.

Further, as an auxiliary solvent, an organic solvent having a boilingpoint of 30° C. or more, preferably in the range of from 50° C. to about160° C. may be used. Typical examples of the auxiliary solvent includeethyl acetate, butyl acetate, ethyl propionate, methyl ethyl ketone,cyclohexane, 2-ethoxyethyl acetate and dimethylformamide.

All or a part of the auxiliary solvent may be removed from an emulsifieddispersion by means of a vacuum distillation, a noodle washing, anultrafiltration, or the like, as occasion demands for the purpose ofimproving storage stability with the lapse of time in the state of theemulsified dispersion, or inhibiting a fluctuation in photographicproperties or improving storage stability with the lapse of time of thefinal coating composition in which the emulsified dispersion is mixedwith a silver halide emulsion.

The average particle size of the oleophilic fine particle dispersionthus obtained is preferably in the range of 0.001 to 1.0 μm, morepreferably in the range of 0.05 to 0.30 μm, and most preferably in therange of 0.08 to 0.20 μm. The average particle size can be determinedwith a measuring device such as Coulter submicron particle analyzermodel N4 (trade name, made by Coulter Electronics Co., Ltd.). If theaverage particle size of the oleophilic fine particles dispersion is toolarge, such problems easily arise that a color-formation efficiency of acoupler is lessened, or gloss on the surface of a light-sensitivematerial deteriorates. In contrast, if the average particle size is toosmall, viscosity of the dispersion increases and consequently a handlingbecomes difficult at the time of production.

The amount to be used (in terms of mass ratio) of a dispersion ofoleophilic fine particles composed of the coupler of the presentinvention to a dispersion medium is preferably in the range of 2 to 0.1,more preferably in the range of 1.0 to 0.2, per 1 part by mass of thedispersion medium. Examples of the dispersion medium include gelatinthat is a typical example, and in addition thereto mention can be madeof hydrophilic polymers, such as polyvinyl alcohol. The oleophilicfine-particle dispersion may contain various compounds, together withthe coupler of the present invention, according to the purpose of use.

Other known photographic materials and additives may be used in thesilver halide photographic light-sensitive material of the presentinvention.

For example, as a photographic support (base), any one of a transmissivetype support and a reflective type support may be used. As thetransmissive type support, it is preferred to use transparent supports,such as a cellulose nitrate film, and a transparent film of polyethyleneterephthalate, or a polyester of 2,6-naphthalenedicarboxylic acid (NDCA)and ethylene glycol (EG), or a polyester of NDCA, terephthalic acid andEG, provided thereon with an information-recording layer such as amagnetic layer. As the reflective type support, it is especiallypreferable to use a reflective support having a substrate laminatedthereon with a plurality of polyethylene layers or polyester layers(water-proof resin layers or laminate layers), at least one of whichcontains a white pigment such as titanium oxide.

A more preferable reflective support for use in the present invention isa support having a paper substrate provided with a polyolefin layerhaving fine holes, on the same side as silver halide emulsion layers.The polyolefin layer may be composed of multi-layers. In this case, itis more preferable for the support to be composed of a fine hole-freepolyolefin (e.g., polypropylene, polyethylene) layer adjacent to agelatin layer on the same side as the silver halide emulsion layers, anda fine hole-containing polyolefin (e.g., polypropylene, polyethylene)layer closer to the paper substrate. The density of the multi-layer orsingle-layer of polyolefin layer(s) existing between the paper substrateand photographic constituting layers is preferably in the range of 0.40to 1.0 g/ml, more preferably in the range of 0.50 to 0.70 g/ml. Further,the thickness of the multi-layer or single-layer of polyolefin layer(s)existing between the paper substrate and photographic constitutinglayers is preferably in the range of 10 to 100 μm, more preferably inthe range of 15 to 70 μm. Further, the ratio of thickness of thepolyolefin layer(s) to the paper substrate is preferably in the range of0.05 to 0.2, more preferably in the range 0.1 to 0.5.

Further, it is also preferable for enhancing rigidity (mechanicalstrength) of the reflective support, by providing a polyolefin layer onthe surface of the foregoing paper substrate opposite to the side of thephotographic constituting layers, i.e., on the back surface of the papersubstrate. In this case, it is preferable that the polyolefin layer onthe back surface be polyethylene or polypropylene, the surface of whichis matted, with the polypropylene being more preferable. The thicknessof the polyolefin layer on the back surface is preferably in the rangeof 5 to 50 μm, more preferably in the range of 10 to 30 μm, and furtherthe density thereof is preferably in the range of 0.7 to 1.1 g/ml. As tothe reflective support for use in the present invention, preferableembodiments of the polyolefin layer provide on the paper substrateinclude those described in JP-A-10-333277, JP-A-10-333278,JP-A-11-52513, JP-A-11-65024, European Patent Nos. 0880065 and 0880066.

Further, it is preferred that the above-described waterproof resin layercontains a fluorescent whitening agent. Further, the fluorescentwhitening agent also may be dispersed in a hydrophilic colloid layer ofthe light-sensitive material. Preferred fluorescent whitening agentsthat can be used, include benzoxazole series, coumarin series, andpyrazoline series compounds. Further, fluorescent whitening agents ofbenzoxazolylnaphthalene series and benzoxazolylstilbene series are morepreferably used. The amount of the fluorescent whitening agent to beused is not particularly limited, and preferably in the range of 1 to100 mg/m². When a fluorescent whitening agent is mixed with awater-proof resin, a mixing ratio of the fluorescent whitening agent tobe used to the water-proof resin is preferably in the range of 0.0005 to3% by mass, and more preferably in the range of 0.001 to 0.5% by mass ofthe resin.

Further, a transmissive type support or the foregoing reflective typesupport each having coated thereon a hydrophilic colloid layercontaining a white pigment may be used as the reflective type support.

Furthermore, a reflective type support having a mirror plate reflectivemetal surface or a secondary diffusion reflective metal surface may beemployed as the reflective type support.

As the support for use in the light-sensitive material of the presentinvention, a support of the white polyester type, or a support providedwith a white pigment-containing layer on the same side as the silverhalide emulsion layer, may be adopted for display use. Further, it ispreferable for improving sharpness that an antihalation layer isprovided on the silver halide emulsion layer side or the reverse side ofthe support. In particular, it is preferable that the transmissiondensity of support is adjusted to the range of 0.35 to 0.8 so that adisplay may be enjoyed by means of both transmitted and reflected raysof light.

In the light-sensitive material of the present invention, in order toimprove, e.g., sharpness of an image, a dye (particularly anoxonole-series dye) that can be discolored by processing, as describedin European Patent No. 0337490 A2, pages 27 to 76, is preferably addedto the hydrophilic colloid layer such that an optical reflection densityat 680 nm in the light-sensitive material is 0.70 or more. It is alsopreferable to add 12% by mass or more (more preferably 14% by mass ormore) of titanium oxide that is surface-treated with, for example,dihydric to tetrahydric alcohols (e.g., trimethylolethane) to awater-proof resin layer of the support.

The light-sensitive material of the present invention preferablycontains, in their hydrophilic colloid layers, dyes (particularlyoxonole dyes and cyanine dyes) that can be discolored by processing, asdescribed in European Patent No. 0337490 A2, pages 27 to 76, in order toprevent irradiation or halation or to enhance safelight safety(immunity) or the like. Further, dyes described in European Patent No.0819977 are also preferably used in the present invention.

Among these water-soluble dyes, some deteriorate color separation orsafelight safety when used in an increased amount. Preferable examplesof the dye which can be used and which does not deteriorate colorseparation include water-soluble dyes described in JP-A-5-127324,JP-A-5-127325 and JP-A-5-216185.

In the present invention, it is possible to use a colored layer that canbe discolored during processing, in place of the water-soluble dye, orin combination with the water-soluble dye. The colored layer capable ofbeing discolored with a processing to be used may contact with alight-sensitive emulsion layer directly, or indirectly through aninterlayer containing an agent for preventing color-mixing duringprocessing, such as hydroquinone and gelatin. The colored layer ispreferably provided as a lower layer (closer to a support) with respectto the light-sensitive emulsion layer that develops the same primarycolor as the color of the colored layer. It is possible to providecolored layers independently, each corresponding to respective primarycolors. Alternatively, only one layer or some layers selected from theabove colored layers may be provided. In addition, it is possible toprovide a colored layer subjected to coloring so as to match a pluralityof primary-color regions. With respect to the optical reflection densityof the colored layer, at the wavelength which provides the highestoptical density in a range of wavelengths used for exposure (a visiblelight region from 400 nm to 700 nm for an ordinary printer exposure, andthe wavelength of the light generated from the light source in the caseof scanning exposure), the optical density is preferably within therange of 0.2 to 3.0, more preferably 0.5 to 2.5, and particularlypreferably 0.8 to 2.0.

The colored layer described above may be formed by a known method. Forexample, there are a method in which a dye in a state of a dispersion ofsolid fine particles is incorporated in a hydrophilic colloid layer, asdescribed in JP-A-2-282244, from page 3, upper right column to page 8,and JP-A-3-7931, from page 3, upper right column to page 11, left undercolumn; a method in which an anionic dye is mordanted in a cationicpolymer, a method in which a dye is adsorbed onto fine grains of silverhalide or the like and fixed in the layer, and a method in which acolloidal silver is used, as described in JP-A-1-239544. As to a methodof dispersing fine-powder of a dye in solid state, for example,JP-A-2-308244, pages 4 to 13 describes a method in which solid fineparticles of dye which is at least substantially water-insoluble at thepH of 6 or less, but at least substantially water-soluble at the pH of 8or more, are incorporated. The method of mordanting an anionic dye in acationic polymer is described, for example, in JP-A-2-84637, pages 18 to26. U.S. Pat. Nos. 2,688,601 and 3,459,563 disclose a method ofpreparing colloidal silver for use as a light absorber. Among thesemethods, preferred are the methods of incorporating fine particles ofdye and of using colloidal silver.

Silver halide grains in the silver halide emulsion which can be used inthe present invention, are preferably cubic or tetradecahedral crystalgrains substantially having {100} planes (these grains may be rounded atthe apexes thereof and further may have planes of higher order), oroctahedral crystal grains. Alternatively, a silver halide emulsion inwhich the proportion of tabular grains having an aspect ratio of 2 ormore and composed of {100} or {111} planes accounts for 50% or more interms of the total projected area, can also be preferably used. The term“aspect ratio” refers to the value obtained by dividing the diameter ofthe circle having an area equivalent to the projected area of anindividual grain by the thickness of the grain. In the presentinvention, cubic grains, or tabular grains having {100} planes as majorfaces, or tabular grains having {111} planes as major faces arepreferably used.

As a silver halide emulsion which can be used in the present invention,for example, a silver chloride, silver bromide, silver iodobromide, orsilver chloro(iodo)bromide emulsion may be used. It is preferable for arapid processing to use a silver chloride or silver chlorobromideemulsion having a silver chloride content of 95 mole % or greater, morepreferably a silver halide emulsion having a silver chloride content of98 mole % or greater. Especially preferred of these silver halideemulsions are those containing silver chloride grains having a silverbromide localized phase on the surface thereof, since both highsensitivity and stabilization of photographic properties are attained.

The silver bromide localized phase is preferably formed by epitaxialgrowth of the localized phase having a total silver bromide content ofat least 10 mole % in the silver bromide localized phase. A silverbromide content of the silver bromide localized phase is preferably inthe range of 10 to 60 mole %, and most preferably in the range of 20 to50 mole %. The silver bromide localized phase is preferably composed ofsilver having population of 0.1 to 5 mole %, more preferably 0.3 to 4mole %, to the molar amount of entire silver which constitutes silverhalide grains for use in the present invention. The silver bromidelocalized phase is preferably doped with complex ions of a metal ofGroup VIII in the periodic table, such as iridium (III) chloride,iridium (III) bromide, iridium (IV) chloride, sodium hexachloroiridate(III), potassium hexachloroiridate (IV), hexaammineiridium (IV) salts,trioxalatoiridium (III) salt, and trioxalatoiridium (IV) salt. Theamount of these compounds to be added can be varied in a wide rangedepending on the purposes for use, and it is preferably in the range of10⁻⁹ to 10⁻² mole, per mole of silver halide.

In a silver halide emulsion for use in the present invention, variouskinds of polyvalent metal ion impurities other than iridium may beincorporated, during grain formation or in the course of physicalripening of the emulsion. As for examples of the impurities to be used,salts or complex salts of metals of Group VIII of the periodic table,such as iron, ruthenium, osmium, rhenium, rhodium, cadmium, zinc, lead,copper and thallium, may be used in combination thereof. In the presentinvention, compounds of metals, such as iron, ruthenium, osmium andrhenium, which have at least four cyano ligands, are particularlypreferred, since high-illumination-intensity sensitivity is furtherenhanced and latent-image sensitization is also inhibited. Iridiumcompounds provide an outstanding effect on the high-illuminationintensity exposure suitability. The amount of these compounds to beadded can be varied in a wide range depending on the purposes, and it ispreferably in the range of 10⁻⁹ mole to 10⁻² mole, per mole of silverhalide.

The silver halide grains contained in the silver halide emulsion for usein the present invention have an average grain size (the grain sizeherein refers to the diameter of a circle equivalent to the projectedarea of an individual grain, and the number average is taken as theaverage grain size) of preferably from 0.1 μm to 2 μm.

With respect to the distribution of sizes of these grains, a so-calledmonodisperse emulsion having a variation coefficient (the value obtainedby dividing the standard deviation of the grain size distribution by theaverage grain size) of 20% or less, more preferably 15% or less, andfurther preferably 10% or less, is preferred. For obtaining widelatitude, it is also preferred to blend the above-described monodisperseemulsions in the same layer or to form a multilayer structure bymultilayer-coating of the monodisperse emulsions.

Various compounds or precursors thereof can be contained in the silverhalide emulsion for use in the present invention to prevent fogging fromoccurring or to stabilize photographic performance during manufacture,storage or photographic processing of the photographic material.Specific examples of compounds useful for the above purposes aredisclosed in JP-A-62-215272, pages 39 to 72, and they can be preferablyused. In addition, 5-arylamino-1,2,3,4-thiatriazole compounds (in whichthe aryl residual group has at least one electron-attractive group), asdisclosed in European Patent No. 0447647, are also preferably used.

Further, in the present invention, in order to enhance stability of thesilver halide emulsion, it is preferable to use hydroxamic acidderivatives described in JP-A-11-109576, cyclic ketones having a doublebond both ends of which are substituted with an amino group or ahydroxyl group, in adjacent to a carbonyl group, as described inJP-A-11-327094 (particularly those represented by formula (SI) and thedescriptions of paragraph numbers 0036 to 0071 of JP-A-11-327094 can beincorporated herein by reference), catechols and hydroquinones eachsubstituted with a sulfo group, as described in JP-A-11-143011 (e.g.,4,5-dihydroxy-1,3-benzenedisulfonic acid,2,5-dihydroxy-1,4-benzenedisulfonic acid, 3,4-dihydroxybenzenesulfonicacid, 2,3-dihydroxybenzenesulfonic acid, 2,5-dihydroxybenzenesulfonicacid, 3,4,5-trihydroxybenzenesulfonic acid, and salts thereof),water-soluble reducing agents represented by any of formulae (I) to(III) of JP-A-11-102045, and hydroxylamines represented by the formula(A) in U.S. Pat. No. 5,556,741 (the descriptions of column 4, line 56 tocolumn 11, line 22 in the U.S. Pat. No. 5,556,741 can be preferablyapplied to the present invention, and incorporated herein by reference).

Spectral sensitization is generally carried out, for the purpose ofimparting spectral sensitivity in a desired light wavelength region tothe light-sensitive emulsion in each layer of the photographic materialof the present invention.

Spectral sensitizing dyes which are used in the photographic material ofthe present invention for spectral sensitization of blue, green and redlight regions, include, for example, those disclosed by F. M. Harmer, inHeterocyclic Compounds—Cyanine Dyes and Related Compounds, John Wiley &Sons, New York, London (1964). Specific examples of the compounds andspectral sensitization processes that are preferably used in the presentinvention include those described in JP-A-62-215272, from page 22, rightupper column to page 38. In addition, the spectral sensitizing dyesdescribed in JP-A-3-123340 are very preferred as red-sensitive spectralsensitizing dyes for silver halide emulsion grains having a high silverchloride content from the viewpoint of stability, adsorption strengthand the temperature dependency of exposure, and the like.

The amount of these spectral sensitizing dyes to be added can be variedin a wide range depending on the occasion, and it is preferably in therange of 0.5×10−6 mole to 1.0×10−2 mole, more preferably in the range of1.0×10⁻⁶ mole to 5.0×10⁻³ mole, per mole of silver halide.

The silver halide emulsion that can be used in the present invention isgenerally chemically sensitized. Chemical sensitization can be performedby utilizing a sulfur sensitization, represented by the addition of anunstable sulfur compound, noble metal sensitization represented by goldsensitization, and reduction sensitization, each singly or incombination thereof. Compounds that are preferably used in chemicalsensitization include those described in JP-A-62-215272, from page 18,right lower column to page 22, right upper column. Of these chemicalsensitization, gold-sensitized silver halide emulsion are particularlypreferred, since fluctuation in photographic properties which occurswhen scanning exposure to laser beams or the like is conducted, can befurther reduced by gold sensitization. In order to conduct goldsensitization, compounds such as chloroauric acid or a salt thereof,gold thiocyanates, gold thiosulfates, and colloidal gold sulfide may beused. The amount of these compounds to be added can be varied in a widerange depending on the occasion, and it is generally in the range of5×10⁻⁷ mole to 5×10⁻³ mole, preferably in the range of 1.0×10⁻⁶ mole to1×10⁻⁴ mole, per mole of silver halide. In the present invention, goldsensitization may be used in combination with other sensitizing methods,for example, sulfur sensitization, selenium sensitization, telluriumsensitization, reduction sensitization, or noble metal sensitizationusing a noble metal compound other than gold compounds.

The silver halide photographic light-sensitive material of the presentinvention can be used for a color negative film, a color positive film,a color reversal film, a color reversal photographic printing paper, acolor photographic printing paper and the like. Among these materials,the light-sensitive material of the present invention is preferably usedfor a color photographic printing paper.

The color photographic printing paper preferably has at least one yellowcolor-forming silver halide emulsion layer, at least one magentacolor-forming silver halide emulsion layer, and at least one cyancolor-forming silver halide emulsion layer, on a support. Generally,these silver halide emulsion layers are in the order, from the support,of the yellow color-forming silver halide emulsion layer, the magentacolor-forming silver halide emulsion layer and the cyan color-formingsilver halide emulsion layer.

However, another layer arrangement which is different from the above,may be adopted.

When, for example, the coupler represented by formula (I) functions as ayellow coupler, a yellow coupler-containing silver halide emulsion layermay be disposed at any position on a support. However, in the case wheresilver halide tabular grains are contained in the yellowcoupler-containing layer, it is preferable that the yellowcoupler-containing layer is positioned more apart from a support than atleast one of a magenta coupler-containing silver halide emulsion layerand a cyan coupler-containing silver halide emulsion layer. Further, itis preferable that the yellow coupler-containing silver halide emulsionlayer is positioned most apart from a support of other silver halideemulsion layers, from the viewpoint of color-development acceleration,desilvering acceleration, and reduction in a residual color due to asensitizing dye. Further, it is preferable that the cyancoupler-containing silver halide emulsion layer is disposed in themiddle of other silver halide emulsion layers, from the viewpoint ofreduction in a blix fading. On the other hand, it is preferable that thecyan coupler-containing silver halide emulsion layer is the lowestlayer, from the viewpoint of reduction in a light fading. Further, eachof a yellow-color-forming layer, a magenta-color-forming layer and acyan-color-forming layer may be composed of two or three layers. It isalso preferable that a color-forming layer is formed by disposing asilver halide emulsion-free layer containing a coupler in adjacent to asilver halide emulsion layer, as described in, for example,JP-A-4-75055, JP-A-9-114035, JP-A-10-246940, and U.S. Pat. No.5,576,159.

Preferred examples of silver halide emulsions and other materials(additives or the like) for use in the present invention, photographicconstitutional layers (arrangement of the layers or the like), andprocessing methods for processing the photographic materials andadditives for processing are disclosed in JP-A-62-215272, JP-A-2-33144and European Patent No. 0355660 A2. Particularly, those disclosed inEuropean Patent No. 0355660 A2 are preferably used. Further, it is alsopreferred to use silver halide color photographic light-sensitivematerials and processing methods therefor disclosed in, for example;JP-A-5-34889, JP-A-4-359249, JP-A-4-313753, JP-A-4-270344, JP-A-5-66527,JP-A-4-34548, JP-A-4-145433, JP-A-2-854, JP-A-1-158431, JP-A-2-90145,JP-A-3-194539, JP-A-2-93641 and European Patent Publication No. 0520457A2.

In particular, as the above-described reflective support and silverhalide emulsion, as well as the different kinds of metal ions to bedoped in the silver halide grains, the storage stabilizers orantifogging agents of the silver halide emulsion, the methods ofchemical sensitization (sensitizers), the methods of spectralsensitization (spectral sensitizing dyes), the cyan, magenta, and yellowcouplers and the emulsifying and dispersing methods thereof, thedye-image stability-improving agents (stain inhibitors and discolorationinhibitors), the dyes (colored layers), the kinds of gelatin, the layerstructure of the light-sensitive material, and the film pH of thelight-sensitive material, those described in the patent publications asshown in the following Table 1 are preferably used in the presentinvention. TABLE 1 Element JP-A-7-104448 JP-A-7-77775 JP-A-7-301895Reflective-type Column 7, line 12 to Column 35, line 43 to Column 5,line 40 to bases Column 12, line 19 Column 44, line 1 Column 9, line 26Silver halide Column 72, line 29 to Column 44, line 36 to Column 77,line 48 to emulsions Column 74, line 18 Column 46, line 29 Column 80,line 28 Different metal Column 74, lines 19 to Column 46, line 30 toColumn 80, line 29 to ion species 44 Column 47, line 5 Column 81, line 6Storage Column 75, lines 9 to Column 47, lines 20 to Column 18, line 11to stabilizers or 18 29 Column 31, line 37 antifoggants (Especially,mercaptoheterocyclic compounds) Chemical Column 74, line 45 to Column47, lines 7 to Column 81, lines 9 to 17 sensitizing Column 75, line 6 17methods (Chemical sensitizers) Spectrally Column 75, line 19 to Column47, line 30 to Column 81, line 21 to sensitizing Column 76, line 45Column 49, line 6 Column 82, line 48 methods (Spectral sensitizers) Cyancouplers Column 12, line 20 to Column 62, line 50 to Column 88, line 49to Column 39, line 49 Column 63, line 16 Column 89, line 16 Yellowcouplers Column 87, line 40 to Column 63, lines 17 to Column 89, lines17 to 30 Column 88, line 3 30 Magenta couplers Column 88, lines 4 toColumn 63, line 3 to Column 31, line 34 to 18 Column 64, line 11 Column77, line 44 and column 88, lines 32 to 46 Emulsifying and Column 71,line 3 to Column 61, lines 36 to Column 87, lines 35 to 48 dispersingColumn 72, line 11 49 methods of couplers Dye-image- Column 39, line 50to Column 61, line 50 to Column 87, line 49 to preservability Column 70,line 9 Column 62, line 49 Column 88, line 48 improving agents(antistaining agents) Anti-fading agents Column 70, line 10 to Column71, line 2 Dyes (coloring Column 77, line 42 to Column 7, line 14 toColumn 9, line 27 to layers) Column 78, line 41 Column 19, line 42, andColumn 18, line 10 Column 50, line 3 to Column 51, line 14 Kind ofgelatins Column 78, lines 42 to Column 51, lines 15 to Column 83, lines13 48 20 to 19 Layer construction Column 39, lines 11 to Column 44,lines 2 to 35 Column 31, line 38 to of light-sensitive 26 Column 32,line 33 materials Film pH of light- Column 72, lines 12 to sensitivematerials 28 Scanning exposure Column 76, line 6 to Column 49, line 7 toColumn 82, line 49 to Column 77, line 41 Column 50, line 2 Column 83,line 12 Preservatives in Column 88, line 19 to developing solutionColumn 89, line 22

As other cyan, magenta and yellow couplers which can be used incombination in the present invention, those disclosed in JP-A-62-215272,page 91, right upper column line 4 to page 121, left upper column line6, JP-A-2-33144, page 3, right upper column line 14 to page 18, leftupper column bottom line, and page 30, right upper column line 6 to page35, right under column, line 11, European Patent No. 0355,660 (A2), page4 lines 15 to 27, page 5 line 30 to page 28 bottom line, page 45 lines29 to 31, page 47 line 23 to page 63 line 50, are also advantageouslyused.

Further, it is preferred for the present invention to add compoundsrepresented by formula (II) or (III) in WO 98/33760 or compoundsrepresented by formula (D) described in JP-A-10-221825.

In the silver halide photographic light-sensitive material of thepresent invention, the dye-forming coupler represented by theabove-described formula (I) may be used singly or in combination of twoor more. In the case where the coupler of formula (I) is used as ayellow coupler, examples of another yellow coupler(s) which may bepreferably used in combination with the above coupler of the presentinvention, include acylacetoamide-type yellow couplers in which the acylgroup has a 3-membered to 5-memberd cyclic structure, such as thosedescribed in European Patent No.0447969 μl; malonic acid dianilide-typeyellow couplers having a cyclic structure, as described in EuropeanPatent No.0482552A1; pyrrol-2- or 3-yl-, or indole-2- or3-yl-carbonylacetic acid anilide-series couplers, as described inEuropean Patent Nos. 0953870A1, 0953871A1, 0953872A1, 0953873A1,0953874A1 and 0953875A1; acylacetamide-type yellow couplers having adioxane structure, as those described in U.S. Pat. No. 5,118,599; inaddition to the compounds described in the above-mentioned table. Aboveall, acylacetamide-type yellow couplers in which the acyl group is an1-alkylcyclopropane-1-carbonyl group, or malonic acid dianilide-typeyellow couplers in which one anilide constitutes an indoline ring isespecially preferably used in combination with the above coupler offormula (I) of the present invention.

The cyan coupler that can be used in the present invention is preferablya phenol-series or naphthol-series cyan coupler, or a heterocycliccoupler.

The phenol coupler is preferably, for example, the cyan couplerrepresented by formula (ADF), as described in JP-A-10-333297, as well asany coupler in the above-mentioned table.

A 2,5-diacylaminophenol coupler, which is improved in hue and fastnessof the resulting dye and which is described in U.S. Pat. No. 5,888,716,is preferably used.

As the heterocyclic coupler, the followings are preferred to use incombination with the coupler of the present invention: pyrroloazole-typecyan couplers described in EP 0488248 and EP0491197A1, andpyrazoloazole-type cyan couplers having a hydrogen bond group or anelectron withdrawing group at its 6 position, as described in U.S. Pat.No. 4,873,183 and No. 4,916,051, particularly preferablypyrazoloazole-type cyan couplers having a carbamoyl group at its 6position, as described in JP-A-8-171185, JP-A-8-311360 andJP-A-8-339060.

Among these cyan couplers, pyrroloazole-series cyan couplers representedby formula (I), as described in JP-A-11-282138, are particularlypreferred. The descriptions in paragraph Nos. 0012 to 0059 of thispublication, as well as the exemplified cyan couplers (1) to (47), canbe applied to the present invention, and are preferably incorporatedherein by reference.

In addition, the coupler of the present invention can also be usedtogether with a diphenylimidazole-series cyan coupler described inJP-A-2-33144; a 3-hydroxypyridine-series cyan coupler (particularly a2-equivalent coupler formed by allowing a coupler (42) of a 4-equivalentcoupler to have a chlorine splitting-off group, and couplers (6) and(9), enumerated as specific examples are preferable) described in EP0333185 A2; a cyclic active methylene-series cyan coupler (particularlycouplers 3, 8, and 34 enumerated as specific examples are preferable)described in JP-A-64-32260; a pyrrolopyrazole-type cyan couplerdescribed in European Patent No. 0456226 Al; or a pyrroloimidazole-typecyan coupler described in European Patent No. 0484909.

As the magenta coupler that can be used in the present invention, usecan be made of a 5-pyrazolone-series magenta coupler or apyrazoloazole-series magenta coupler, such as those described in theabove-mentioned patent publications in the above Table. Among these,preferred are pyrazolotriazole couplers in which a secondary or tertiaryalkyl group is directly bonded to the 2-, 3- or 6-position of thepyrazolotriazole ring, as described in JP-A-61-65245; pyrazoloazolecouplers having a sulfonamido group in its molecule, as described inJP-A-61-65246; pyrazoloazole couplers having an alkoxyphenylsulfonamidoballasting group, as described in JP-A-61-147254; and pyrazoloazolecouplers having an alkoxy or aryloxy group on its 6-position, asdescribed in European Patent Nos. 0226849 A2 and 0294785 A, in view ofthe hue and stability of image to be formed therefrom and color-formingproperty of the couplers.

Particularly as the magenta coupler, pyrazoloazole couplers representedby formula (M-I), as described in JP-A-8-122984, are preferred. Thedescriptions of paragraph Nos. 0009 to 0026 of the patent publicationcan be entirely applied to the present invention and therefore areincorporated herein by reference.

In addition, pyrazoloazole couplers having a steric hindrance group atboth the 3- and 6-positions, as described in European Patent Nos. 854384and 884640, are also preferably used.

It is preferred that magenta or cyan couplers, as well as the (yellow)coupler of the present invention, are also pregnated into a loadablelatex polymer (as described, for example, in U.S. Pat. No. 4,203,716) inthe presence (or absence) of the high-boiling-point organic solventdescribed in the foregoing table, or they are dissolved in the presence(or absence) of the foregoing high-boiling-point organic solvent with apolymer insoluble in water but soluble in an organic solvent, and thenemulsified and dispersed into an aqueous hydrophilic colloid solution.

The water-insoluble but organic solvent-soluble polymers that can bepreferably used, include the homo-polymers and co-polymers disclosed inU.S. Pat. No. 4,857,449, from column 7 to column 15 and WO 88/00723,from page 12 to page 30. The use of methacrylate-series oracrylamide-series polymers, especially acrylamide-series polymers aremore preferable in view of color-image stabilization and the like.

To suppress Blix discoloration (leuco dye reciprocity failure) by ableaching solution or bleach-fixing solution, it is preferred to use apolymer described in JP-A-8-62797, JP-A-9-171240 and JP-A-9-329861, inthe hydrophilic colloid layer.

In the present invention, known color mixing-inhibitors may be used.Among these compounds, those described in the following patentpublications are preferred.

For example, high molecular weight redox compounds described inJP-A-5-333501; phenidone- or hydrazine-series compounds as described in,for example, WO 98/33760 and U.S. Pat. No. 4,923,787; and white couplersas described in, for example, JP-A-5-249637, JP-A-10-282615 and GermanPatent No. 19629142 A1, may be used. Further, in order to acceleratedeveloping speed by increasing the pH of a developing solution, redoxcompounds described in, for example, German Patent Nos. 19,618,786 A1and 19,806,846 A1, European Patent Nos. 0,839,623 A1 and 0,842,975 A1,and French Patent No. 2,760,460 A1, are also preferably used.

In the present invention, as an ultraviolet ray absorbent, it ispreferred to use compounds having a high molar extinction coefficient.Examples of these compounds include those having a triazine skeleton.Among these compounds, use can be made of those described, for example,in JP-A-46-3335, JP-A-55-152776, JP-A-5-197074, JP-A-5-232630,JP-A-5-307232, JP-A-6-211813, JP-A-8-53427, JP-A-8-234364,JP-A-8-239368, JP-A-9-31067, JP-A-10-115898, JP-A-10-147577,JP-A-10-182621, JP-T-8-501291 (“JP-T” means searched and publishedInternational patent application), European Patent No. 0,711,804 A1 andGerman Patent No. 19,739,797A.

In the present invention, examples of a decoloration inhibitor(anti-fading agent), a hue adjusting agent, and the like other thanthose described in the above Table, include vinyl compounds representedby formula (II), aniline derivatives represented by formula (III) havingan oxygen-nitrogen bond or substituted with an alkoxy group,non-diffusible phenydone derivatives represented by formula (IV),nondiffusion carboxylic acids represented by formula (V), non-diffusiblearylcarbamoyl derivatives represented by formula (VI), arylamidederivatives represented by formula (VII), and cyclic imide derivativesrepresented by formula (VIII), each of which are described inJP-A-11-258748, and all of them can be preferably used.

As the binder or protective colloid that can be used in thelight-sensitive material of the present invention, gelatin is usedadvantageously, but another hydrophilic colloid can be used singly or incombination with gelatin. It is preferable for the gelatin for use inthe present invention that the content of heavy metals, such as Fe, Cu,Zn and Mn, as impurities therein, is reduced to 5 ppm or below, morepreferably 3 ppm or below.

Further, the amount of calcium contained in the light-sensitive materialis preferably 20 mg/m² or less, more preferably 10 mg/m² or less, andmost preferably 5 mg/m² or less.

In the present invention, it is preferred to add an antibacterial(fungi-preventing) agent and antimold agent, as described inJP-A-63-271247, in order to destroy various kinds of molds and bacteriawhich propagate in a hydrophilic colloid layer and deteriorate theimage.

Further, the pH of the film of the light-sensitive material ispreferably in the range of 4.0 to 7.0, more preferably in the range of4.0 to 6.5.

The light-sensitive material of the present invention can preferably beused, in addition to the printing system using a general negativeprinter, in a scanning exposure system using a cathode ray tube (CRT).

The cathode ray tube exposure apparatus is simpler and more compact, andtherefore less expensive than a laser-emitting apparatus. Further,optical axis and color (hue) can easily be adjusted.

In a cathode ray tube that is used for image-wise exposure, variouslight-emitting substances which emit a light in the spectral region, areused as occasion demands. For example, any one of red-light-emittingsubstances, green-light-emitting substances, blue-light-emittingsubstances, or a mixture of two or more of these light-emittingsubstances may be used. The spectral regions are not limited to theabove red, green and blue, and fluorophoroes which can emit a light in aregion of yellow, orange, purple or infrared can be used. Particularly,a cathode ray tube that emits a white light by means of a mixture ofthese light-emitting substances is often used.

In the case where the light-sensitive material has a plurality oflight-sensitive layers each having different spectral sensitivitydistribution from each other and also the cathode ray tube hasfluorescent substances which emit light in a plurality of spectralregions, exposure to a plurality of colors may be carried out at thesame time. Namely, color image signals may be input into a cathode raytube, to allow light to be emitted from the surface of the tube.Alternatively, a method in which an image signal of each of colors issuccessively input and light of each of colors is emitted in order, andthen exposure is carried out through a film capable of cutting a colorother than the emitted color, i.e., a surface successive exposure, maybe used. Generally, among these methods the surface successive exposureis preferred from the viewpoint of high quality enhancement, because acathode ray tube having high resolution can be used.

The light-sensitive material of the present invention can preferably beused in the digital scanning exposure system using monochromatic highdensity light, such as a gas laser, a light-emitting diode, asemiconductor laser, a second harmonic generation light source (SHG)comprising a combination of nonlinear optical crystal with asemiconductor or a solid state laser using a semiconductor laser as anexcitation light source. It is preferred to use a semiconductor laser,or a second harmonic generation light source (SHG) comprising acombination of nonlinear optical crystal with a solid state laser or asemiconductor laser, to make a system more compact and inexpensive. Inparticular, to design a compact and inexpensive apparatus having alonger duration of life and high stability, use of a semiconductor laseris preferable; and it is preferred that at least one of exposure lightsources should be a semiconductor laser.

When such a scanning exposure light source is used, the maximum spectralsensitivity wavelength of the light-sensitive material of the presentinvention can be arbitrarily set up in accordance with the wavelength ofa scanning exposure light source to be used. Since oscillationwavelength of a laser can be made half, using a SHG light sourceobtainable by a combination of a nonlinear optical crystal with asemiconductor laser or a solid state laser using a semiconductor as anexcitation light source, blue light and green light can be obtained.Accordingly, it is possible to have the spectral sensitivity maximum ofa photographic material in normal three wavelength regions of blue,green and red.

The exposure time in such a scanning exposure is defined as the timenecessary to expose the size of the picture element (pixel) with thedensity of the picture element being 400 dpi, and preferred exposuretime is 10 sec or less and more preferably 10 sec or less.

The scanning exposure system that can preferably be used for the presentinvention is described in detail in the patent publications as shown inthe above table.

With respect to the processing of the photographic material of thepresent invention, processing materials and processing methods, asdisclosed in JP-A-2-207250, from page 26, right under column, line 1 topage 34, right upper column, line 9, and JP-A-4-97355, from page 5, leftupper column, line 17 to page 18, right under column, line 20, can bepreferably applied. Further, as preservatives which are used in thedeveloping solution, compounds described in the patent publications asshown in the above table can be preferably used.

The present invention is preferably applied to a light-sensitivematerial having rapid processing suitability.

The term “color-developing time” as used herein refers to a period oftime required from the beginning of dipping a light-sensitive materialinto a color-developing solution until the light-sensitive material isdipped into a blix solution in the subsequent processing step. In thecase where a processing is carried out using, for example, anautoprocessor, the color-developing time is the sum total of a time inwhich a light-sensitive material has been dipped in a color-developingsolution (so-called “time in the solution”) and a time in which thelight-sensitive material has been conveyed in air toward a bleach-fixingbath in the step subsequent to color development (so-called “time in theair”). Likewise, the term “blix time” as used herein refers to a periodof time required from the beginning of dipping a light-sensitivematerial into a blix solution until the light-sensitive material isdipped into a washing bath or a stabilizing bath in the subsequentprocessing step. Further, the term “washing or stabilizing time” as usedherein refers to a period of time required from the beginning of dippinga light-sensitive material into a washing solution or a stabilizingsolution until the end of the dipping toward a drying step (so-called“time in the solution”).

In the present invention, the color-developing time is preferably 60 secor less, more preferably from 50 sec to 6 sec, further preferably from30 sec to 6 sec. Likewise, the blix time is preferably 60 sec or less,more preferably from 50 sec to 6 sec, further preferably from 30 sec to6 sec. Further, the washing or stabilizing time is preferably 150 sec orless, more preferably from 130 sec to 6 sec.

Examples of a development method applicable to the photographic materialof the present invention after exposure, include a conventional wetsystem, such as a development method using a developing solutioncontaining an alkali agent and a developing agent, and a developmentmethod wherein a developing agent is incorporated in the photographicmaterial and an activator solution, e.g., a developing agent-freealkaline solution is employed for the development, as well as a heatdevelopment system using no processing solution. In particular, theactivator method using a developing agent-free alkaline solution ispreferred over the other methods, because the processing solutioncontains no developing agent, thereby it enables easy management andhandling of the processing solution, and reduction in waste disposalload to make for environmental preservation.

The preferable developing agents or their precursors to be incorporatedin the photographic materials in the case of adopting the activatormethod include the hydrazine compounds described in, for example,JP-A-8-234388, JP-A-9-152686, JP-A-9-152693, JP-A-9-211814 andJP-A-9-160193.

Further, the processing method in which the photographic materialreduced in the amount of silver to be applied undergoes the imageamplification processing using hydrogen peroxide (intensificationprocessing), can be employed preferably. In particular, it is preferablyto apply this processing method to the activator method. Specifically,the image-forming methods utilizing an activator solution containinghydrogen peroxide, as disclosed in JP-A-8-297354 and JP-A-9-152695 canbe preferably used.

The processing with an activator solution is generally followed by adesilvering step in the activator method, but the desilvering step canbe omitted in the case of applying the image amplification processingmethod to photographic materials of a low silver amount. In such a case,washing or stabilization processing can follow the processing with anactivator solution to result in simplification of the processingprocess. On the other hand, when the system of reading the imageinformation from photographic materials by means of a scanner or thelike is employed, the processing form requiring no desilvering step canbe applied, even if the photographic materials are those of a highsilver amount, such as photographic materials for shooting.

The activator solution, desilvering solution (bleach-fixingingsolution), washing solution and stabilizing solution for use in thepresent invention can contain known ingredients and can be used inconventional manners. Preferably, those described in ResearchDisclosure, Item 36544, pp. 536-541 (September 1994), and JP-A-8-234388can be used in the present invention.

It is preferred to use a band stop filter, as described in U.S. Pat. No.4,880,726, when the photographic material of the present invention issubjected to exposure with a printer. Color mixing of light can beexcluded and color reproducibility is remarkably improved by the abovemeans.

In the present invention, a yellow microdot pattern may be previouslyformed by pre-exposure before giving an image information, to therebyperform copy restraint, as described in European Patent Nos. 0789270 A1and 0789480 A1.

The light-sensitive material of the present invention can be preferablyused as a light-sensitive material for the advanced photo-system, whichhas a magnetic recording layer. The light-sensitive material of thepresent invention can be preferably used in a system wherein a smallamount of water is used to perform heat-development, or in a completedry system wherein no water is used to perform heat-development.Detailed descriptions on these systems are found, for example, inJP-A-6-35118, JP-A-6-17528, JP-A-56-146133, JP-A-60-119557, andJP-A-1-161236.

In the present invention, the wording “a silver halide photographiclight-sensitive material” means to include not only a light-sensitivematerial for forming a color image but also a light-sensitive materialfor forming a monotone image, an example of which is a black and whiteimage.

In case where the coupler of the present invention is applied to a colorpaper, light-sensitive material and the like described in JP-A-11-7109,particularly descriptions in paragraph numbers 0071 to 0087 inJP-A-11-7109 are preferable, and therefore the above descriptions inJP-A-11-7109 are incorporated herein by reference.

In case where the coupler of the present invention is applied to a colornegative film, the descriptions at paragraph Nos. 0115 to 0217 of thespecification of JP-A-11-305396 can be preferably applied thereto, andtherefore incorporated herein by reference.

In case where the coupler of the present invention is applied to a colorreversal film, the descriptions at paragraph Nos. 0018 to 0021 of thespecification of JP-A-11-84601 can be preferably applied thereto, andtherefore incorporated herein by reference.

(Azomethine Dye)

First, the compound represented by formula (IIA) of the presentinvention, among the compounds represented by formula (II) (herein theyare also referred to as azomethine dye compounds) of the presentinvention, are explained in detail.

In formula (IIA), R₁₁, Q and X each have the same meanings as defined informula (IA). Preferable examples of these R₁₁, Q and X are also thesame as those in formula (IA).

In formula (IIA), R₅ and R₆ each represent a hydrogen atom or asubstituent, or R₅ and R₆ may bond with each other to form a ring; R₇represents a hydrogen atom or a substituent. n represents 0 (zero) or aninteger of 1 to 4. When R₅, R₆ and R₇ each represent a substituent,examples of the substituent are the same as those exemplified above asthe substituent that R₁₁ may have.

R₇s may be the same or different independently, or R₇s may be combinedtogether to form a condensed ring, when n is 2 or more. Alternatively R₇may bond together with R₅ or R₆ to form a condensed ring, n is 1 ormore.

R₇ is preferably a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 30 carbon atoms, a substituted or unsubstitutedalkenyl group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 30 carbon atoms, a halogen atom,or a substituted or unsubstituted acylamino group having 1 to 30 carbonatoms, more preferably a hydrogen atom or an alkyl group. Furthermorepreferably, R₇ is a methyl group at the ortho position to theazomethine-nitrogen atom.

R₅ and R₆ each are preferably a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms or a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, more preferably an alkyl group. Furthermorepreferably, one of R₅ and R₆ is an ethyl group, and the other is a2-hydroxyethyl group or a 2-methanesulfonamidoethyl group.

Preferable specific examples of the azomethine dye represented byformula (IIA) according to the present invention are shown below.However, the present invention should not be construed as being limitedto these compounds.

The compounds represented by formula (IIA) according to the presentinvention can be synthesized by a coupling reaction of the compoundrepresented by formula (IA) according to the present invention, with anoxidized product of a phenylenediamine-series developing agent(particularly an N,N-di-substituted-p-phenylenediamine derivative).Besides, the compound of the formula (IIA) can be synthesized byreaction of the compound represented by formula (IA) in which Y is ahydrogen atom, with a 4-nitrosoaniline-series compound. Specificsynthesis of the compounds is explained in the Examples described below.

Next, the compounds represented by formula (IIB), among the compoundsrepresented by formula (II) of the present invention, are explained indetail.

In formula (IIB), R₁, R₄, Q and X each have the same meanings as definedin formula (IB). Preferable examples of R₁, R₄, Q and X are also thesame as those in formula (IB).

In formula (IIB), R₅ and R₆ each represent a hydrogen atom or asubstituent, or R₅ and R₆ may bond with each other to form a ring; R₇represents a hydrogen atom or a substituent. n represents 0 (zero) or aninteger of 1 to 4. When R₅, R₆ and R₇ each represent a substituent,examples of the substituent are the same as those of R₄ described above.

R₇s may be the same or different-independently, or R₇s may be combinedtogether to form a condensed ring, when n is 2 or more. Alternatively R₇may be combined together with R₅ or R₆ to form a condensed ring, when nis 1 or more.

R₇ is preferably a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 30 carbon atoms, a substituted or unsubstitutedalkenyl group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 30 carbon atoms, a halogen atom,or a substituted or unsubstituted acylamino group having 1 to 30 carbonatoms, more preferably a hydrogen atom and an alkyl group. Furthermorepreferably, R₇ is a methyl group at the ortho position to theazomethine-nitrogen atom.

R₅ and R₆ each are preferably a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms or a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, more preferably an alkyl group. Furthermorepreferably, one of R₅ and R₆ is an ethyl group, and the other is a2-hydroxyethyl group or a 2-methanesulfonamidoethyl group.

Preferable specific examples of the azomethine dye represented byformula (IIB) according to the present invention are shown below.However, the present invention should not be construed as being limitedto these compounds.

The compounds represented by formula (IIB) according to the presentinvention can be synthesized by a coupling reaction of the compoundrepresented by formula (IB) according to the present invention, with anoxidized product of a phenylenediamine-series developing agent(particularly an N,N-di-substituted-p-phenylenediamine derivative).Besides, the compound of formula (IIB) can be synthesized by reaction ofthe compound represented by formula (IB) according to the presentinvention in which Y is a hydrogen atom, with a 4-nitrosoaniline-seriescompound. Specific synthesis of the compounds is explained in theExamples described below.

The azomethine dye compounds of the present invention, which areexcellent in both hue and fastness, can be used in many fields.Particularly the azomethine dye compounds are useful for the ink,dyestuffs, and the like. Further, the azomethine dye compounds areuseful as an image-forming dye, for example, dyestuffs for the ink whichis used for an ink-jet printer. Besides, the azomethine dye compoundsare useful as dyestuffs for color photography.

According to the present invention, can be provided a dye-formingcoupler that gives a dye having an excellent hue and an excellentstorage stability. Further, in addition to the above, according to thepresent invention, can also be provided a dye-forming coupler that givesa dye having an excellent hue, especially an excellent sharpness at thefoot portion of a peak in interest of the absorption curve at the longerwavelength side, and that can be produced at a low production cost owingto reduced steps. Furthermore, in addition to the above, according tothe present invention, can also be provided a dye-forming coupler thatgives a dye having a large molecular extinction coefficient, anexcellent storage stability, especially an excellent light-fastness, andthat can be produced at a low production cost owing to reduced steps.

Further, according to the present invention, can be provided a silverhalide photographic light-sensitive material that exhibits bothexcellent color reproducibility and dye-image fastness, by adding thecoupler in the light-sensitive material. Furthermore, in addition to theabove, according to the present invention, can be also provided a silverhalide photographic light-sensitive material that exhibits goodsharpness.

Still further, according to the present invention, can be provided anazomethine dye compound having both excellent hue and storage stability.Further, in addition to the above, according to the present invention,can be also provided an azomethine dye compound having a large molecularextinction coefficient.

The present invention will now be described in more detail withreference to the following examples, but the invention is not limited tothose.

EXAMPLES Comparative Examples 1 to 2

1. Preparation of a Dye for Comparison (CD-1)

To a mixture of 0.85 g of the following coupler for comparison (C-1),0.80 g of N-ethyl-N-(β-methanesulfoneamidoethyl)-3-methyl-4-aminoanilinesulfate, 3.75 g of sodium carbonate, 60 ml of THF and 50 ml of water,was gradually added a solution of 1.45 g of ammonium persulfatedissolved in 10 ml of water, at room temperature under stirring. Thereaction liquid was stirred for 1 hour and then the THF phase wasseparated. The THF phase was purified by silica gel chromatography, togive a dye for comparison (CD-1), which was the following yellowazomethine dye for comparison.Coupler for Comparison (C-1)

Dye for Comparison (CD-1)

2. Preparation of A Dye for Comparison (CD-2)

To a mixture of 0.73 g of the following coupler for comparison (C-2)(Compound (2) described in U.S. Pat. No. 5,455,149), 0.80 g ofN-ethyl-N-(β-methanesulfonamidoethyl)-3-methyl-4-aminoaniline sulfate,3.75 g of sodium carbonate, 60 ml of THF and 50 ml of water, a solutionof 1.45 g of ammonium persulfate dissolved in 10 ml of water wasgradually added with stirring at room temperature. After stirring thereaction mixture at 60° C. for 10 minutes, the THF layer was separatedand purified by silica gel column chromatography, to obtain a dye forcomparison (CD-2) which was a yellow azomethine dye for comparison asshown below.

Coupler for Comparison (C-2)

(Compound (2) Described in U.S. Pat. No. 5,455,149)

Dye for Comparison (CD-2)

Examples 1 to 4

1. Preparation of Dyes (D-1) to (D-4)

The following dyes: D-1 (wherein the coupler (1) was used), D-2 (whereinthe coupler (2) was used), D-3 (wherein the coupler (20) was used), andD-4 (wherein the coupler (30) was used), which were azomethine dyecompounds obtained from the dye-forming couplers of the presentinvention, were synthesized in the same manner as the “Preparation of adye for comparison (CD-2)” in Comparative Example 2, except forreplacing the coupler for comparison (C-2) with the above-shownexemplified coupler (1), coupler (2), coupler (20) and coupler (30) ofthe present invention, respectively.

Measurement of Absorption Spectrum

Using each of the dyes for comparison (CD-1) and (CD-2) and the dyes(D-1) to (D-4) of the present invention, each of which was obtained inComparative Examples 1 and 2 and Examples 1 to 4 described above,absorption spectra were measured in the following manner. 1.5 mg of anyone of the dyes for comparison (CD-1) and (CD-2) and the dyes (D-1) to(D-4) was precisely weighed in a 100-ml measuring flask. 100 ml of ethylacetate was added to dissolve the dye. Each resulting solution wasdiluted with ethyl acetate, to prepare a sample solution 101 containingthe dye for comparison (CD-1), a sample solution 102 containing the dyefor comparison (CD-2), a sample solution 103 containing the dye (D-1), asample solution 104 containing the dye (D-2), a sample solution 105containing the dye (D-3), and a sample solution 106 containing the dye(D-4), respectively.

Each of the thus-obtained sample solutions 101 to 106 was placed in 1-cmthick-quartz cell, and visible absorption spectrum was measured by anultraviolet-visible spectrophotometer, manufactured by ShimadzuCorporation. Further, as the parameter that expresses the sharpness atthe foot portion of a peak in interest of the absorption curve at thelonger wavelength side of the dye to be used, ΔS (0.05)/nm of each dyewas obtained, according to the following manner. Assuming thatabsorbance (A) of the maximum absorption wavelength (γmax) is 1, thewavelength (γ(0.05)) corresponding to A=0.05 at the longer wavelengthside was measured. The ΔS (0.05)/nm is obtained by calculation accordingto the following expression:ΔS(0.05)=λmax−γ(0.05)

The results that were obtained by the above calculation, are shown inTable 2. TABLE 2 Sample Kind of Kind of No. Coupler Dye ΔS(0.05)/nmRemarks 101 Coupler for CD-1 78.0 Comparative comparison Example (C-1)102 Coupler for CD-2 74.2 Comparative comparison Example (C-2) 103Coupler (1) D-1 72.9 This invention 104 Coupler (2) D-2 70.6 Thisinvention 105 Coupler (20) D-3 70.3 This invention 106 Coupler (30) D-471.2 This invention

From the results shown in Table 2, it is understood that the dyesobtained from the dye-forming couplers of the present invention exhibitsmaller ΔS (0.05)/nm than those obtained from dye-forming couplers forcomparison, which means that the dyes of the present invention areexcellent in sharpness at the foot portion of a peak of the absorptioncurve at the longer wavelength side. In other words, in a silver halidephotographic light-sensitive material containing the coupler of thepresent invention, only a small portion of a reddish tinge is mixed in ayellow dye obtained from the coupler, resulting in improvement in colorreproducibility of the obtained image (particularly colorreproducibility of lemon yellow).

Test of Fading Resistance of Dyes to an Acid

With respect to each of the dyes for comparison (CD-1) and (CD-2) andthe dyes (D-1) to (D-4), which were obtained in Comparative Examples 1and 2 and Examples 1 to 4 described above, a test of fading resistanceto an acid was carried out in the following manner. 1.0 mg of any one ofthe dyes for comparison (CD-1) and (CD-2) and the dyes (D-1) to (D-4)was dissolved in 15 ml of NMP (1-methyl-2-pyrrolidinone; purity forpeptide synthesis: 99%), to prepare a sample solution 201 containing thedye for comparison (CD-1), a sample solution 202 containing the dye forcomparison (CD-2), a sample solution 203 containing the dye (D-1), asample solution 204 containing the dye (D-2), a sample solution 205containing the dye (D-3), and a sample solution 206 containing the dye(D-4), respectively.

0.49 g of boric acid, 8 ml of 1-normal acetic acid aqueous solution and16 ml of 1-normal phosphoric acid aqueous solution were mixed in a200-ml measuring flask, to prepare a solution (Britton-Robinson buffersolution; hereinafter referred to as “B. R. buffer A solution” forshort). Then, phosphoric acid was added to the resulting solution and pHwas adjusted to 1.15, and then the temperature of the solution wasmaintained at 60° C. The resulting buffer solution was added to thepreviously prepared sample solutions 201 to 206 until the total amountwould become 25 ml. Then, visible absorption spectra of thethus-obtained solutions directly after the preparation by adding thebuffer solution to the sample solutions, and after 4 hour storage at aconstant temperature of 60° C., were measured, by means ofultraviolet-visible spectrometer, manufactured by Shimadzu Corporation.Absorbance of each of the solutions at the maximum absorption wavelengthwas calculated respectively.

The rate of density (the remaining ratio: %) was calculated in the ratioof absorbance of a sample before the test of fading resistance to anacid and absorbance of the same sample after the test of fadingresistance to an acid. The resultant remaining ratio was utilized as anevaluation indicator of fastness of the dye to an acid. The results thatwere obtained are shown in Table 3. TABLE 3 Sample Kind of Kind ofRemaining No. Coupler Dye ratio (%) Remarks 201 Coupler for CD-1 15Comparative comparison Example (C-1) 202 Coupler for CD-2 94 Comparativecomparison Example (C-2) 203 Coupler (1) D-1 98 This invention 204Coupler (2) D-2 98 This invention 205 Coupler (20) D-3 99 This invention206 Coupler (30) D-4 98 This invention

It is apparent from the Table 3 that the dye obtained from thedye-forming coupler of the present invention is remarkably excellent infastness of the dye to an acid.

Comparative Example 3

1. Preparation of Emulsified Dispersion of Coupler for Comparison (C-1)

0.88 g of coupler for comparison (C-1) and 2.6 g of tricresyl phosphatewere dissolved with heating in 10 ml of ethyl acetate. The resultingsolution is referred to as an oil phase solution. Separately, 4.2 g ofgelatin was added to 25 ml of water at room temperature and swelledsufficiently. Thereafter, the gelatin mixture was heated to 40° C. andcompletely dissolved. To the resulting aqueous gelatin solution kept atabout 40° C., 3 ml of 5% aqueous sodium dodecylbenzenesulfonate solutionand the previously prepared oil phase solution were added. Then, theresulting mixture was emulsified dispersed by a homogenizer, to preparethe emulsified dispersion of coupler for comparison (C-1).

2. Preparation of Light-Sensitive Material for Comparison

A coating solution having the composition described below, including thepreviously prepared emulsified dispersion of coupler for comparison(C-1), was prepared. On a polyethylene laminate paper having anundercoat layer, the thus-obtained coating solution was coated so thatthe coating amounts of the silver halide emulsion and the coupler became0.33 mmol/m² (in terms of silver) and 1 mmol/m², respectively.Furthermore, a gelatin was coated as a protective layer so that thecoating amount of gelatin became 2 g/m². Thus, Sample 301 of alight-sensitive material for comparison, was prepared.

(Composition of Coating Solution) Emulsion: Silver Chlorobromide 13 g(cubic grains in which 0.3 mole % in total of silver bromide was locallycontained in a portion of the grain surface and the substrate was silverchloride with average grain size of 60 μm. To spectrally sensitize thisemulsion, each of sensitizing dyes A, B and C was added in 1.4 × 10⁻⁴mole per mole of silver halide, respectively) 10% Gelatin 28 gEmulsified Dispersion of the above-described Coupler for comparison(C-1) 22 g Water 37 ml 4% Aqueous Solution of Sodium1-Hydroxy-3,5-dichloro-s-triazine 5 ml

Comparative Example 4

1. Preparation of Emulsified Dispersion of Coupler for Comparison (C-2)

Emulsified dispersion of Coupler for comparison (C-2) was prepared inthe same manner as the “1: Preparation of Emulsified Dispersion ofCoupler for comparison (C-1)” in Comparative Example 3, except forreplacing the Coupler for comparison (C-1) with the Coupler forcomparison (C-2) (Compound (2) described in U.S. Pat. No. 5,455,149).

2. Preparation of Light-Sensitive Material for Comparison

Light-sensitive material for comparison sample 302 was prepared in thesame manner as the “2. Preparation of Light-sensitive material forcomparison” in Comparative Example 3, except for replacing theemulsified dispersion of Coupler for comparison (C-1) with theemulsified dispersion of Coupler for comparison (C-2) (Compound (2)described in U.S. Pat. No. 5,455,149).

Examples 5 to 8

1. Preparation of each of Emulsified Dispersions of Couplers (1), (2),(20) and (30)

Each of emulsified dispersions of couplers according to the presentinvention was prepared in the same manner as the “1. Preparation ofEmulsified Dispersion of Coupler for comparison (C-1)” in ComparativeExample 3, except for replacing the coupler for comparison (C-1) withthe foregoing exemplified couplers (1), (2), (20) and (30) of thepresent invention, respectively.

2. Preparation of Light-Sensitive Material of the Present Invention

In the same manner as in “2. Preparation of Light-sensitive material forcomparison” in Comparative Example 3, Sample 303 (use was made of thecoupler (1)), Sample 304 (use was made of the coupler (2)), Sample 305(use was made of the coupler (20)), Sample 306 (use was made of thecoupler (30)), each of which was the light-sensitive material of thepresent invention, were prepared, except for replacing the emulsifieddispersion of Coupler for comparison(C-1) with the emulsifieddispersions of the foregoing exemplified couplers (1), (2), (20) and(30) of the present invention, respectively.

Evaluation Tests of Color-Image Fastness

Using the samples 301 to 306 which were obtained in the foregoingComparative Examples 3 to 4 and Examples 5 to 8, the evaluation tests ofcolor-image fastness was carried out in the following way.

First, each of the samples was wedge-wise exposed to a white light, andthen subjected to color-development processing according to theprocessing steps as shown below.

(Processing Steps) Step Temperature Time Color-developing 38.5° C. 45seconds Bleach-fixing 30 to 36° C. 45 seconds Stabilization (1) 30 to37° C. 20 seconds Stabilization (2) 30 to 37° C. 20 secondsStabilization (3) 30 to 37° C. 20 seconds Drying 70 to 85° C. 70 seconds

The respective steps of the color developing, the bleach-fixing, and thestabilization (1), (2) and (3) were carried out by immersing each of thesamples into the following respective processing solutions under theabove-mentioned conditions. (Color-developing solution in thecolor-developing step) Water 800 ml Dimethylpolysiloxane-seriessurfactant 0.1 g (Silicone KF351A (trade name), manufactured byShin-Etsu Chemical Co., Ltd.) Triethanolamine 11.6 gEthylenediaminetetraacetic acid 4.0 g Sodium4,5-dihydroxybenzene-1,3-disulfonate 0.5 g Potassium chloride 10.0 gPotassium bromide 0.040 g Triazinylaminostylbene-series fluorescentwhitening agent 2.5 g (Hakkol FWA-SF (trade name), manufactured by ShowaChemicals Inc.) Sodium sulfite 0.1 g DisodiumN,N-bis(sulfonatoethyl)hydroxylamine 8.5 gN-ethyl-N-(β-methanesulfonamidoethyl)- 5.0 g3-methyl-4-aminoaniline.3/2.sulfate.monohydrate Potassium carbonate 26.3g Water to make 1000 ml pH (adjusted with potassium hydroxide 10.15 andsulfuric acid at 25° C.) (Bleach-fixing solution in the bleach-fixingstep) Water 800 ml Iron (III) ammonium ethylenediaminetetraacetate 47.0g Ethylenediaminetetraacetic acid 1.4 g m-Carboxymethylbenzenesulfinicacid 8.3 g Nitric acid (67%) 16.5 g Imidazole 14.6 g Ammoniumthiosulfate aq. solution (750 g/liter) 107 ml Ammonium sulfite 16.0 gPotassium metabisulfite 23.1 g Water to make 1000 ml pH (adjusted withacetic 6.0 acid and ammonia at 25° C.) (Stabilizing solution in thestabilization (1) to (3) steps) Sodium chlorinated-isocyanurate 0.02 gDeionized water 1000 ml (electroconductivity: 5 μS/cm or less) pH 6.5

The processed samples each colored yellow. Each of the light-sensitivematerial, samples 303 to 306 according to the present invention gave thedye image having a sharper hue than those of light-sensitive materialfor comparison, samples 301 to 302.

Then, each of the color developing-processed samples 301 to 306 wasirradiated with Xenon light source (100,000 lux) with intermittentillumination under the conditions of light for 5 hours/darkness for 1hour, for 14 days, and light-fastness of the dye image was evaluated.The density after irradiation at a portion where the initial densityD=1.0 is indicated as the remaining ratio in percent. The results thatwere obtained are shown in Table 4.

As is apparent from Table 4, it is understood that the light-sensitivematerials of the present invention are excellent in light-fastness.TABLE 4 Sample Kind of Kind of Remaining No. Coupler Dye ratio (%)Remarks 301 Coupler for CD-1 85 Comparative comparison Example (C-1) 302Coupler for CD-2 74 Comparative comparison Example (C-2) 303 Coupler (1)D-1 92 This invention 304 Coupler (2) D-2 90 This invention 305 Coupler(20) D-3 93 This invention 306 Coupler (30) D-4 91 This invention

Example 9

After corona discharge treatment was performed on the surface of a papersupport whose both surfaces were laminated with polyethylene resin, agelatin undercoat layer containing sodium dodecylbenzenesulfonate wasformed on that surface. In addition, photographic constituting layersfrom the first layer to the seventh layer were successively coated onthe support, to make a silver halide color photographic light-sensitivematerial (sample 001) having the following layer arrangement. Thecoating solution for each of the photographic constituting layers wasprepared as follows.

(Preparation of Coating-Solution for First Layer)

62 g of a yellow coupler (ExY), 8 g of a dye-image stablilizer (Cpd-1),4 g of a dye-image stabilizer (Cpd-2), 8 g of a dye-image stabilizer(Cpd-3) and 2 g of a dye-image stabilizer (Cpd-8) were dissolved in 23 gof a solvent (Solv-1) and 80 ml of ethyl acetate. The resultant solutionwas added to 220 g of 23.5% by mass gelatin aqueous solution containing4 g of sodium dodecylbenzenesulfonate. The resultant mixture wasemulsified and dispersed by a high speed stirring emulsifier (DISOLVER),followed by addition of water, to prepare 900 g of emulsified dispersionA.

Separately, a silver chlorobromide emulsion A (cubic, a 3:7 mixture (Agmolar ratio) of a large-size emulsion A with an average grain size of0.72 μm and a small-size emulsion A with an average grain size of 0.60μm. The variation coefficients of grain size distributions of thelarge-size and the small-size emulsions were 0.08 and 0.10,respectively. Each emulsion consisted of silver halide grains in which0.3 mole % of AgBr was locally contained in a portion of the grainsurface and the substrate was silver chloride) was prepared.

To this emulsion, were added blue-sensitive sensitizing dyes A, B and Cshown below in 1.4×10⁻⁴ mole for the large-size emulsion and 1.7×10⁻⁴mole for the small-size emulsion per mole of silver halide,respectively. Chemical ripening of this emulsion was carried outoptimally, by adding a sulfur sensitizer and a gold sensitizer.

The emulsified dispersion A described above and this silverchlorobromide emulsion A were mixed and dispersed, to prepare a coatingsolution of the first layer having the following composition. Thecoating amount of each silver halide emulsion is in terms of silver.

(Preparation of Coating-Solutions for Second layer to Seventh Layer)

The coating solutions for the second to seventh layers were prepared inthe similar manner as for the coating solution of the first layer.1-oxy-3,5-dichloro-s-triazine sodium salt was used as a gelatin hardenerin each layer. In addition, Ab-1, Ab-2, Ab-3 and Ab-4 were added to eachlayer such that their total amounts were 15.0 mg/m², 60.0 mg/m², 5.0mg/m² and 10.0 mg/m², respectively. (Ab-1) Antiseptic (Ab-2) Antiseptic

(Ab-3) Antiseptic (Ab-4) Antiseptic

R₁ R₂ a —CH₃ —NHCH₃ b —CH₃ —NH₂ c —H —NH₂ d —H —NHCH₃

A mixture in 1:1:1:1 (molar ratio) of a, b, c, and d

For the silver chlorobromide emulsion of the respective light-sensitiveemulsion layer, the following spectral sensitizing dyes were used.Blue-sensitive emulsion layer

(The sensitizing dyes A, B, and C were added to the large-size emulsionin an amount of 1.4×10⁻⁴ mol, respectively per mol of silver halide, andto the small-size emulsion in an amount of 1.7×10⁻⁴ mol, respectivelyper mol of silver halide.)Green-Sensitive Emulsion Layer

(The sensitizing dye D was added to the large-size emulsion in an amountof 3.0×10⁻⁴ mol, and to the small-size emulsion in an amount of 3.6×10⁻⁴mol, per mol of the silver halide; the sensitizing dye E was added tothe large-size emulsion in an amount of 4.0×10⁻⁵ mol, and to thesmall-size emulsion in an amount of 7.0×10⁻⁵ mol, per mol of the silverhalide; and the sensitizing dye F was added to the large-size emulsionin an amount of 2.0×10⁻⁴ mol, and to the small-size emulsion in anamount of 2.8×10⁻⁴ mol, per mol of the silver halide.)Red-Sensitive Emulsion Layer

(The sensitizing dyes G, and H were added to the large-size emulsion inan amount of 6.0×10⁻⁵ mol, respectively per mol of silver halide, and tothe small-size emulsion in an amount of 9.0×10⁻⁵ mol, respectively permol of silver halide.)

Further, the following compound I was added to the red-sensitiveemulsion layer in an amount of 2.6×10⁻³ mol per mol of the silverhalide.

Further, to the blue-sensitive emulsion layer, the green-sensitiveemulsion layer, and the red-sensitive emulsion layer, was added1-(3-methylureidophenyl)-5-mercaptotetrazole in amounts of 3.3×10⁻⁴ mol,1.0×10⁻³ mol, and 5.9×10⁻⁴ mol, respectively, per mol of the silverhalide. Further, the compound was also, added to the second layer, theforth layer, the sixth layer, and the seventh layer, in amounts of 0.2mg/m², 0.2 mg/m² , 0.6 mg/m ², and 0.1 mg/m², respectively.

Further, to the blue-sensitive emulsion layer and the green-sensitiveemulsion layer, was added 4-hydroxy-6-methyl-1,3,3a,7-tetrazaindene inamounts of 1×10 mol and 2×10⁻⁴ mol, respectively, per mol of the silverhalide.

Further, to the red sensitive emulsion layer, was added a copolymer ofmethacrylic acid and butyl acrylate (1:1 in mass ratio; averagemolecular weight, 200,000 to 400,000) in an amount of 0.05 g/m Further,to the second layer, the fourth layer, and the sixth layer, was added amixture of disodium catechol-3,5-disulfonate and2,6-bishydroxyamino-4-dimetylamino-1,3,5-triazine (9:1 in molar ratio)in amounts of 6 mg/m², 6 mg/m², and 18 mg/m², respectively.

Further, in order to prevent irradiation, the following dyes (coatingamounts are shown in parentheses) were added to the emulsion layers.

(Layer Constitution)

The composition of each layer is shown below. The numbers show coatingamounts (g/m²). In the case of the silver halide emulsion, the coatingamount is in terms of silver.

Support

Polyethylene-Resin Laminated Paper

{The polyethylene resin on the first layer side contained a whitepigment (TiO₂; content of 16 mass %, Zno; content of 4 mass %), afluorescent whitening agent (a mixture of 4,4′-bis(benzoxazolyl)stilbeneand 4,4′-bis(5-methylbenzoxazolyl)stilbene mixed in a ratio of 8/2;content of 0.05 mass %) and a bluish dye (ultramarine)}

First Layer (Blue-Sensitive Emulsion Layer) A silver chlorobromideemulsion A (cubic, a 3:7 0.26 mixture of a large-size emulsion A havingan average grain size of 0.72 μm, and a small-size emulsion A having anaverage grain size of 0.60 μm (in terms of mol of silver). The deviationcoefficients of the grain size distribution were 0.08 and 0.10,respectively. Each emulsion had 0.3 mol % of silver bromide containedlocally in part of the grain surface whose substrate was made up ofsilver chloride) Gelatin 1.35 Yellow coupler (ExY) 0.62 Color-imagestabilizer (Cpd-1) 0.08 Color-image stabilizer (Cpd-2) 0.04 Color-imagestabilizer (Cpd-3) 0.08 Color-image stabilizer (Cpd-8) 0.02 Solvent(Solv-1) 0.23

Second Layer (Color-Mixing Inhibiting Layer) Gelatin 0.99 Color-mixinginhibitor (Cpd-4) 0.09 Color-mixing inhibiting auxiliary (Cpd-5) 0.018Stabilizer (Cpd-6) 0.13 Color-mixing inhibitor (Cpd-7) 0.01 Solvent(Solv-1) 0.06 Solvent (Solv-2) 0.22

Third Layer (Green-Sensitive Emulsion Layer) A silver chlorobromideemulsion B (cubic, a 1:3 0.14 mixture of a large-size emulsion B havingan average grain size of 0.45 μm, and a small-size emulsion B having anaverage grain size of 0.35 μm (in terms of mol of silver). The deviationcoefficients of the grain size distribution were 0.10 and 0.08,respectively. Each emulsion had 0.4 mol % of silver bromide containedlocally in part of the grain surface whose substrate was made up ofsilver chloride) Gelatin 1.36 Magenta coupler (ExM) 0.15 Ultravioletabsorbing agent (UV-1) 0.05 Ultraviolet absorbing agent (UV-2) 0.03Ultraviolet absorbing agent (UV-3) 0.02 Ultraviolet absorbing agent(UV-4) 0.03 Ultraviolet absorbing agent (UV-6) 0.01 Color-imagestabilizer (Cpd-2) 0.02 Color-mixing inhibitor (Cpd-4) 0.002 Stabilizer(Cpd-6) 0.09 Color-image stabilizer (Cpd-8) 0.02 Color-image stabilizer(Cpd-9) 0.03 Color-image stabilizer (Cpd-10) 0.01 Color-image stabilizer(Cpd-11) 0.0001 Solvent (Solv-3) 0.11 Solvent (Solv-4) 0.22 Solvent(Solv-5) 0.20

Fourth Layer (Color-Mixing Inhibiting Layer) Gelatin 0.71 Color-mixinginhibitor (Cpd-4) 0.06 Color-mixing inhibiting auxiliary (Cpd-5) 0.013Stabilizer (Cpd-6) 0.10 Color-mixing inhibitor (Cpd-7) 0.007 Solvent(Solv-1) 0.04 Solvent (Solv-2) 0.16

Fifth Layer (Red-Sensitive Emulsion Layer) A silver chlorobromideemulsion C (cubic, a 1:4 0.20 mixture of a large-size emulsion C havingan average grain size of 0.50 μm, and a small-size emulsion C having anaverage grain size of 0.41 μm (in terms of mol of silver). The deviationcoefficients of the grain size distribution were 0.09 and 0.11,respectively. Each emulsion had 0.5 mol % of silver bromide containedlocally in part of the grain surface whose substrate was made up ofsilver chloride) Gelatin 1.11 Cyan coupler (ExC-2) 0.13 Cyan coupler(ExC-3) 0.03 Color-image stabilizer (Cpd-1) 0.05 Stabilizer (Cpd-6) 0.05Color-mixing inhibitor (Cpd-7) 0.02 Color-image stabilizer (Cpd-9) 0.04Color-image stabilizer (Cpd-10) 0.01 Color-image stabilizer (Cpd-14)0.01 Color-image stabilizer (Cpd-15) 0.03 Color-image stabilizer(Cpd-16) 0.05 Color-image stabilizer (Cpd-17) 0.05 Color-imagestabilizer (Cpd-18) 0.06 Color-image stabilizer (Cpd-19) 0.06 Solvent(Solv-5) 0.15 Solvent (Solv-8) 0.05 Solvent (Solv-9) 0.10

Sixth Layer (Ultraviolet Absorbing Layer) Gelatin 0.66 Ultravioletabsorbing agent (UV-1) 0.19 Ultraviolet absorbing agent (UV-2) 0.06Ultraviolet absorbing agent (UV-3) 0.06 Ultraviolet absorbing agent(UV-4) 0.05 Ultraviolet absorbing agent (UV-5) 0.08 Ultravioletabsorbing agent (UV-6) 0.01 Solvent (Solv-7) 0.25

Seventh Layer (Protective Layer) Gelatin 1.00 Acryl-modified copolymerof polyvinyl alcohol 0.04 (modification degree: 17%) Liquid paraffin0.02 Surface-active agent (Cpd-13) 0.01

Further, light-sensitive material 401 was made in the same manner as thethus-prepared silver halide color photographic light-sensitive material(001), except for replacing the yellow coupler of the emulsifieddispersion A for the first layer of the silver halide color photographiclight-sensitive material (001) prepared as described above, with thecoupler for comparison (C-1) which was used in the foregoing ComparativeExample 1, in an equivalent molar amount. Likewise, light-sensitivematerial 402 was made in the same manner as above, except for replacingthe yellow coupler with the coupler for comparison (C-2) which was usedin the foregoing Comparative Example 2, in an equivalent molar amount.Further, light-sensitive materials (403) to (408) according to thepresent invention were made in the same manner as above, except forreplacing the yellow coupler with the dye-forming couplers (1), (2),(20), (30), (35) and (40), which included those used in Examples 1 to 4,in an equivalent molar amount, respectively.

Average particle size of each of the above-prepared dispersions oflipophilic fine-particles containing a yellow coupler was in the rangeof 0.10 to 0.20 μm.

The above-described light-sensitive material (001) was stored at 25° C.,55% RH, for 10 days, and then cut into a 127-mm width roll. After that,the roll-like material was exposed to light imagewise and subjected to acontinuous processing (running test) with a mini-Lab printer processor(PP1258 AR, trade name, made by Fuji Photo Film Co., Ltd.) in accordancewith the process mentioned below, until the amount of replenisher to thecolor developer tank became 2 times the tank capacity. ReplenishmentProcessing step Temperature Time rate* Color development  38.5° C. 45sec  45 ml Bleach-fixing  38.0° C. 45 sec  35 ml Rinse (1)  38.0° C. 20sec — Rinse (2)  38.0° C. 20 sec — Rinse (3) **38.0° C. 20 sec — Rinse(4) **38.0° C. 30 sec 121 ml*Replenishment rate per m² of the light-sensitive material to beprocessed.**A rinse cleaning system RC50D, trade name, manufactured by Fuji PhotoFilm Co., Ltd., was installed in the rinse (3), and the rinse solutionwas taken out from the rinse (3) and sent to a reverse osmosis membranemodule (RC50D) by using a pump. The permeated water obtained in thattank was supplied to the rinse (4), and the concentrated water wasreturned to the rinse (3). Pump pressure was controlled such# that the water to be permeated in the reverse osmosis module would bemaintained in an amount of 50 to 300 ml/min, and the rinse solution wascirculated under controlled temperature for 10 hours a day. (The rinsewas made in a tank counter-current system from (1) to (4).)

The composition of each processing solution was as follows. (Tank (Colordeveloper) solution) (Replenisher) Water   800 ml   800 mlDimethylpolysiloxane-series  0.1 g  0.1 g surfactant (Silicone KF351A/trade name, Shin-Etsu Chemical Co., Ltd.) Triethanolamine  11.6 g  11.6g Ethylenediamine tetraacetic acid  4.0 g  4.0 g Sodium4,5-dihydroxybenzene-1,3-  0.5 g  0.5 g disulfonate Potassium chloride 10.0 g — Potassium bromide 0.040 g 0.010 gTriazinylaminostilbene-series  2.5 g  5.0 g fluorescent whitening agent(Hakkol FWA-SF/trade name, Showa Chemical Industry Co., Ltd.) Sodiumsulfite  0.1 g  0.1 g Disodium-N,N-bis(sulfonatoethyl)  8.5 g  11.1 ghydroxylamine N-ethyl-N-(β-  5.0 g  15.7 g methanesulfonamidoethyl)-3-methyl-4-amino-4-aminoaniline 3/2 sulfate 1 hydrate Potassium carbonate 26.3 g  26.3 g Water to make  1000 ml  1000 ml pH (25° C./adjustedusing 10.15 12.50 potassium hydroxide and sulfuric acid)

(Tank (Bleach-fixing solution) solution) (Replenisher) Water   800 ml  800 ml Ammonium iron (III)  47.0 g  94.0 g ethylenediaminetetraacetateEthylenediamine tetraacetic acid  1.4 g  2.8 gm-Carboxymethylbenzenesulfinic  8.3 g  16.5 g acid Nitric acid (67%) 16.5 g  33.0 g Imidazole  14.6 g  29.2 g Ammonium thiosulfate (750 g/l)  107 ml   214 ml Ammonium sulfite  16.0 g  32.0 g Potassiummethbisulfite  23.1 g  46.2 g Water to make  1000 ml  1000 ml pH (25°C./adjusted using acetic  6.0  6.0 acid and ammonia)

(Tank (Rinse solution) solution) (Replenisher) Sodiumchlorinated-isocyanurate  0.02 g  0.02 g Deionized water (conductivity:5 μS/cm  1000 ml  1000 ml or less) PH  6.5  6.5

Then, each of the light-sensitive materials was subjected to gradationexposure via an-optical wedge having a three-color separatingsensitometric filter, using a sensitometer (FWH Model, made by FujiPhoto Film Co., Ltd., its light source has a color temperature of 3200°K.). At that time, the exposure was carried out so that 0.1 second ofthe exposure time gave the exposure amount of 250 lx·sec.

Separately, each of the light-sensitive materials was subjected to thescanning exposure described below.

The scanning exposure was carried out using a scanning exposure deviceillustrated in FIG. 1 of JP-A-8-16238. As the light source, a lightsource of 688 nm (R light) taken out by using a laser semiconductor, alight source of 532 nm (G light) and a light source of 473 nm (B light)each taken out by combining a semiconductor laser with SHG,respectively, were used. The quantity of R light was modulated by anexternal modulator, and laser beams were scan-exposed to a sample movingin the direction vertical to the scanning direction by the reflection toa rotating polyhedron. The scanning pitch was 400 dpi and the averageexposure time per pixel was 8×10⁻⁸sec. The temperature of thesemiconductor laser was kept constant by using a Peltier device toprevent the quantity of light from being changed by temperature.

Each of the exposed samples was processed with the foregoing runningsolution, and then evaluated in the same manner as the light-sensitivematerials in Comparative Examples 3 and 4 and Examples 5 to 8.

The results which were obtained, demonstrate that each of thelight-sensitive materials of the present invention using the dye-formingcouplers of the present invention exhibits a high color-forming propertyand each of the dyes formed from the couplers is excellent in both hueand fastness.

Example 10

A light-sensitive material was made in the same manner as the sample 101in JP-A-11-305396, except for replacing ExY-2 and ExY-3 in the 13thlayer and the 14th layer of the Sample 101 as described inJP-A-11-305396 with the dye-forming coupler (1) according to the presentinvention in an equimolar amount, respectively. The light-sensitivematerial thus obtained was exposed and processed in the same manner asin Example 1 of JP-A-11-305396, and then evaluated according to themethod described in Examples of the present application. The similarresults as in the above-mentioned Example 5 in the present applicationwere obtained.

Example 11

Light-sensitive material was made in the same manner as Sample 107 inExample 1 of JP-A-11-84601, except for replacing the couplers C-5, C-6and C-10 in the 13th layer and the 14th layer, and C-6 and C-10 in the15th layer of the Sample 107 in the Example 1 in JP-A-11-84601, with thedye-forming coupler (1) according to the present invention, in anequimolar amount, respectively. The light-sensitive material thusobtained was exposed and processed in the same manner as in Example 1 ofJP-A-11-84601, and then evaluated according to the method described inExamples of the present application. The similar results as in theabove-mentioned Example 5 in the present application were obtained.

Examples 12 to 15

1. Preparation of Dyes (D-1B) to (D-4B)

The following dyes: D-1B (wherein the coupler (1B) was used), D-2B(wherein the coupler (2B) was used), D-3B (wherein the coupler (20B) wasused), and D-4B (wherein the coupler (30B) was used), which wereazomethine dye compounds obtained from the dye-forming couplers of thepresent invention, were synthesized in the same manner as the“Preparation of a dye for comparison (CD-2)” in the above-mentionedComparative Example 2, except for replacing the coupler for comparison(C-2) with the above-shown exemplified coupler (1B), coupler (2B),coupler (20B) and coupler (30B) of the present invention, respectively.

Measurement of Absorption Spectrum

Using each of the dyes for comparison (CD-1) and (CD-2) which wereobtained in the above-mentioned Comparative Examples 1 and 2, and theDyes (D-1B) to (D-4B) which were obtained in Examples 12 to 15 describedabove, absorption spectra were measured in the following manner.

1.5 mg of any one of the dyes for comparison (CD-1) to (CD-2), and Dyes(D-1B) to (D-4B) was precisely weighed in a 100-ml measuring flask. 100ml of ethyl acetate was added to dissolve the dye. Each resultingsolution was diluted with ethyl acetate, to prepare a sample solution101B containing the dye for comparison (CD-1), a sample solution 102Bcontaining the dye for comparison (CD-2), a sample solution 103Bcontaining the Dye (D-1B), a sample solution 104B containing the Dye(D-2B), a sample solution 105B containing the Dye (D-3B), and a samplesolution 106B containing the Dye (D-4B), respectively.

Each of the thus-obtained sample solutions 101B to 106B was placed in 1cm-thick quartz cell, and visible absorption spectrum was measured by aultraviolet-visible spectrophotometer, manufactured by SimadzuCorporation. Based on the spectrum, each molecular extinctioncoefficient was calculated. Further, as the parameter that expresses thesharpness at the foot portion of a peak of the absorption curve at thelonger wavelength side of the dye to be used, ΔS (0.05)/nm of each thedye to be used was obtained according to the following way. Assumingthat absorbance (A) of the maximum absorption wavelength (λmax) is 1,the wavelength (λ (0.05)) corresponding to A=0.05 at the longerwavelength side was measured. The ΔS (0.05)/nm is obtained bycalculation according to the following expression:ΔS(0.05)=λmax−λ(0.05)

The results that were obtained by the above calculation, are shown inTable 5. TABLE 5 Sample Kind of Kind No. Coupler of Dye ε ΔS(0.05)/nmRemarks 101B Coupler CD-1 1.65 × 10⁴ 78.0 Comparative for Examplecomparison (C-1) 102B Coupler CD-2 2.76 × 10⁴ 74.2 Comparative forExample comparison (C-2) 103B Coupler D-1B 2.82 × 10⁴ 70.3 This (1B)invention 104B Coupler D-2B 2.85 × 10⁴ 64.1 This (2B) invention 105BCoupler D-3B 2.83 × 10⁴ 66.5 This (20B) invention 106B Coupler D-4B 2.81× 10⁴ 68.2 This (30B) invention

From the results in Table 5, it is understood that the dyes obtainedfrom the dye-forming couplers of the present invention exhibit highermolecular extinction coefficient than those obtained from thedye-forming coupler for comparison. This means that the dyes of thepresent invention enables to provide the density of the conventionallevel even in a thinner layer of the light-sensitive material and thelike. It is further understood that the dyes of the present inventionexhibit small ΔS (0.05)/nm, which means that they are excellent insharpness at the foot portion of a peak in interest of the absorptioncurve at the longer wavelength side. In other words, in the silverhalide photographic light-sensitive material containing the coupler ofthe present invention, only a small portion of a reddish tinge was mixedin a yellow dye obtained from the coupler, resulting in improvement innot only color reproduction of the obtained image (particularly colorreproduction of lemon yellow), but also in sharpness.

Test of Fading Resistance of Dyes to an Acid

With respect to each of the above-mentioned dyes for comparison (CD-1)and (CD-2) and the above-mentioned dyes (CD-1B) to (D-4B), the test offading resistance to an acid was carried out in the same manner asdescribed in the above.

Sample solution 201B (wherein the dye for comparison (CD-1) in theabove-mentioned Comparative example 1 was used), Sample solution 202B(wherein the dye for comparison (CD-2) in the above-mentionedComparative example 2 was used), Sample solution 203B (wherein the Dye(D-1B) was used), Sample solution 204B (wherein the dye (D-2B) wasused), Sample solution 205B (wherein the dye for comparison (D-3B) wasused), and Sample solution 206B (wherein the dye (D-4B) was used) wereprepared, respectively, in the same manner as the sample solutions 201to 206 of the above-mentioned Example 1 to 4, except that Dyes (D-1B) to(D-4B) were used in place of Dyes (D-1) to (D-4), respectively. Then, toeach of the thus-obtained sample solutions 201B to 206B, the test offading resistance of dyes to an acid was performed in the same manner asin the above-mentioned Examples 1 to 4.

The results that were obtained are shown in Table 6. TABLE 6 Sample Kindof Kind of Remaining No. Coupler Dye ratio (%) Remarks 201B Coupler forCD-1 15 Comparative comparison Example (C-1) 202B Coupler for CD-2 94Comparative comparison Example (C-2) 203B Coupler D-1B 98 This invention(1B) 204B Coupler D-2B 98 This invention (2B) 205B Coupler D-3B 99 Thisinvention (20B) 206B Coupler D-4B 97 This invention (30B)

It is apparent from the Table 6 that the dye obtained from thedye-forming coupler of the present invention is remarkably excellent infastness of the dye of an acid.

Examples 16 to 19

1. Preparation of each of Emulsified Dispersions of Couplers (1B), (2B),(20B) and (30B)

Each of emulsified dispersions of couplers according to the presentinvention was prepared in the same manner as the “1. Preparation ofEmulsified Dispersion of Coupler for comparison (C-1)” in theabove-described Comparative Example 3, except for replacing the couplerfor comparison (C-1) with the foregoing exemplified couplers (1B), (2B),(20B) and (30B) of the present invention, respectively.

2. Preparation of Light-Sensitive Material of the Present Invention

In the same manner as in “2. Preparation of Light-sensitive material forcomparison” in the above-described Comparative Example 3, Sample 303B(wherein the Coupler (1B) was used), Sample 304B (wherein the Coupler(2B) was used), Sample 305B (wherein the Coupler (20B) was used), Sample306B (wherein the Coupler (30B) was used), each of which was thelight-sensitive material of the present invention, were prepared, exceptfor replacing the emulsified dispersion of Coupler for comparison (C-1)with the emulsified dispersions of the foregoing exemplified couplers(1B), (2B), (20B) and (30B) of the present invention, respectively.

Evaluation Tests of Color-Image Fastness

Using the Samples 303B to 306B which were obtained in the foregoingExamples 16 to 19, and, for comparison, the sample 301B (which is thesame as sample 301 in the above-described Comparative Example 3) and thesample 302B (which is the same as sample 302 in the above-describedComparative Example 4), the evaluation test of color-image fastness wascarried out in the same manner as the samples 301 to 306 which wereobtained in the foregoing Comparative examples 3 and 4 and Examples 5 to8.

First, each of the samples 301B to 306B was wedge-wise exposed to awhite light, and then subjected to color-development processingaccording to the processing steps in the same manner as theabove-described Examples 5 to 8.

The processed samples each colored yellow. Each of the light-sensitivematerial, the samples 303B to 306B according to the present inventiongave the dye image having a sharper hue, as compared to those oflight-sensitive material for comparison, the samples 301B to 302B.

Then, each of the samples 301B to 306B processed for color developmentwas irradiated with Xenon light source (100,000 lux) with intermittentillumination under the conditions of light for 5 hours/darkness for 1hour, for 14 days, and light-fastness of the dye image was evaluated.The density after irradiation at a portion where the initial densityD=1.0 is indicated as the remaining ratio in percent. The results thatwere obtained are shown in Table 7.

As is apparent from Table 7, it is understood that the light-sensitivematerials of the present invention are excellent in light-fastness.TABLE 7 Sample Kind of Kind of Remaining No. Coupler Dye ratio (%)Remarks 301B Coupler for CD-1 85 Comparative comparison Example (C-1)302B Coupler for CD-2 74 Comparative comparison Example (C-2) 303BCoupler (1B) D-1B 93 This invention 304B Coupler (2B) D-2B 91 Thisinvention 305B Coupler (20B) D-3B 94 This invention 306B Coupler (30B)D-4B 91 This invention

Example 20

Light-sensitive material 401B was made in the same manner as the silverhalide color photographic light-sensitive material (001) prepared in theabove-mentioned Example 9, except for replacing the yellow coupler ofthe emulsified dispersion A for the first layer of the silver halidecolor photographic light-sensitive material (001) prepared in theabove-mentioned Example 9, with the coupler for comparison (C-1) whichwas used in the foregoing Comparative Example 1, in an equivalent molaramount. Likewise, light-sensitive material 402B was made in the samemanner as above, except for replacing the yellow coupler with thecoupler for comparison (C-2) which was used in the foregoing ComparativeExample 2, in an equivalent molar amount. Further, light-sensitivematerials (403B) to (408B) according to the present invention were madein the same manner as above, except for replacing the yellow couplerwith the dye-forming couplers (1B), (2B), (20B), (30B), (35B) and (40B),which included those used in Examples 12 to 15, in an equivalent molaramount, respectively.

Average particle of each of the above-prepared dispersions of lipophilicfine-particles containing a yellow coupler was in the range of 0.10 to0.20 μm.

In the same manner as the above-described Example 9, the above-describedlight-sensitive material (001) was subjected to the continuousprocessing (running test).

Then, in the same manner as the above-described Example 9, each of thelight-sensitive material samples (401B) to (408B) was subjected to thegradation exposure.

Separately, each of the light-sensitive material samples (401B) to(408B) was subjected to the scanning exposure in the same manner as theabove-mentioned Example 9.

Each of the exposed samples (401B) to (408B) was processed with theforegoing running solution in the same manner as the above-mentionedExample 9. Then, the 0.25 processed samples were tested and evaluated inthe same manner as in the above-described Comparative examples 3 to 4,Examples 5 to 8, and Examples 16 to 19.

The results which were obtained, demonstrate that each of thelight-sensitive materials of the present invention using the dye-formingcouplers of the present invention exhibits a high color-forming propertyand each of the dyes formed from the couplers is excellent in both hueand fastness.

Example 21

A light-sensitive material was made in the same manner as Sample 101 inJP-A-11-305396, except for replacing the couplers ExY-2 and ExY-3 in the13th layer and the 14th layer of the Sample 101 as described inJP-A-11-305396, with the dye-forming coupler (1B) according to thepresent invention, in an equimolar amount, respectively. Thelight-sensitive material thus obtained was exposed and processed in thesame manner as in Example 1 of JP-A-11-305396, and then evaluatedaccording to the method described in Examples in the presentapplication. The similar results as in the above-mentioned Example 16 inthe present application were obtained.

Example 22

A light-sensitive material was made in the same manner, as Sample 107 inExample 1 in JP-A-11-84601, except for replacing the couplers C-5, C-6and C-10 in the 13th layer and the 14th layer, and C-6 and C-10 in the15th layer of the Sample 107 as described in Example 1 of JP-A-11-84601,with the dye-forming coupler (1B) of the present invention, in anequimolar amount, respectively. The light-sensitive material thusobtained was exposed and processed in the same manner as in Example 1 ofJP-A-11-84601, and then evaluated according to the method described inExamples of the instant application. The similar results as in theabove-mentioned Example 16 in the present application were obtained.

Having described our invention as related to the present embodiments, itis our intention that the invention not be limited by any of the detailsof the description, unless otherwise specified, but rather be construedbroadly within its spirit and scope as set out in the accompanyingclaims.

1. A dye-forming coupler represented by formula (I):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R_(A) represents an arylgroup, a heterocyclic group, or an —(R₁)_(r)—(R₄)_(m) group; Xrepresents an aryl group; Y represents a hydrogen atom, or a group thatis capable of being split-off upon a coupling reaction with an oxidizedproduct of a developing agent: wherein, when R_(A) represents an—(R₁)_(r)—(R₄)_(m) group, R₁ represents a methylene group, a methinegroup, or a carbon atom; r represents an integer of 1 to 30, and R₁s maybe the same or different independently, when r is 2 or more; R₄represents a substituent except for a hydrogen atom; m represents aninteger of 1 to 30, and R₄S may be the same or different independently,or R₄s may be combined together to form a multiple bond, oralternatively R₄s may bond with each other to form a ring, when m is 2or more; and the —(R₁)_(r)—(R₄)_(m) group does not represent astraight-chain alkyl group.
 2. The dye-forming coupler as claimed inclaim 1, wherein the dye-forming coupler represented by formula (I) isrepresented by formula (IA):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R₁₁ represents an arylgroup or a heterocyclic group; X represents an aryl group; Y representsa hydrogen atom, or a group that is capable of being split-off upon acoupling reaction with an oxidized product of a developing agent.
 3. Thedye-forming coupler as claimed in claim 2, wherein, in the dye-formingcoupler represented by formula (IA), Q is a residue that forms, togetherwith the —N—C=N-moiety, a 4-pyrimidone ring.
 4. The dye-forming coupleras claimed in claim 1, wherein the dye-forming coupler represented byformula (I) is represented by formula (IB):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R₁ represents a methylenegroup, a methine group, or a carbon atom; r represents an integer of 1to 30, and R1s may be the same or different independently, when r is 2or more; R₄ represents a substituent except for a hydrogen atom; mrepresents an integer of 1 to 30, and R₄s may be the same or differentindependently, or R₄s may be combined together to form a multiple bond,or alternatively R₄s may bond with each other to form a ring, when m is2 or more; X represents an aryl group; Y represents a hydrogen atom, ora group that is capable of being split-off upon a coupling reaction withan oxidized product of a developing agent; and the —(R₁)_(r)—(R₄)_(m)group does not represent a straight-chain alkyl group.
 5. Thedye-forming coupler as claimed in claim 4, wherein, in the dye-formingcoupler represented by formula (IB), Q is a residue that forms, togetherwith the —N—C═N— moiety, a 4-pyrimidone ring; and R4 is a group selectedfrom the group consisting of an alkyl group, an alkenyl group, an arylgroup, a heterocyclic group, a halogen atom, an amino group, a hydroxylgroup, a carboxyl group, a sulfo group, an acylamino group, an alkyl- orarylsulfonylamino group, a carbamoyl group, a sulfamoyl group, an acylgroup, a sulfonyl group, an alkoxycarbonyl group, an aryloxycarbonylgroup, an alkylthio group, an arylthio group, a cyano group, an alkoxygroup and an aryloxy group.
 6. The dye-forming coupler as claimed inclaim 4, wherein, in the dye-forming coupler represented by formula(IB), at least one R₄ bonds with a carbon atom at at least one α- toδ-positions in the (R₁)_(r).
 7. An azomethine dye compound representedby formula (II):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R_(A) represents an arylgroup, a heterocyclic group, or an —(R₁)_(r)—(R₄)_(m) group; Xrepresents an aryl group; wherein, when R_(A) represents an—(R₁)_(r)—(R₄)_(m) group, R₁ represents a methylene group, a methinegroup, or a carbon atom; r represents an integer of 1 to 30, and R₁s maybe the same or different independently, when r is 2 or more; R₄represents a substituent except for a hydrogen atom; m represents aninteger of 1 to 30, and R₄S may be the same or different independently,or R₄S may be combine together to form a multiple bond, or alternativelyR₄S may bond with each other to form a ring, when m is 2 or more; andthe —(R₁)_(r)—(R₄)_(m) group does not represent a straight-chain alkylgroup; R₅ and R₆ each represent a hydrogen atom or a substituent, or R₅and R₆ may bond with each other to form a ring; R₇ represents a hydrogenatom or a substituent; n represents 0 (zero) or an integer of 1 to 4,with the proviso that R₇s may be the same or different independently, orR₇s may bond with each other to form a condensed ring, n is 2 or more;or R₇ may bond with R₅ or R₆ to form a condensed ring, n is 1 or more.8. The azomethine dye compound as claimed in claim 7, wherein theazomethine dye compound represented by formula (II) is represented byformula (IIA):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R₁₁ represents an arylgroup or a heterocyclic group; X represents an aryl group; R₅ and R₆each represent a hydrogen atom or a substituent, or R₅ and R₆ may bondwith each other to form a ring; R₇ represents a hydrogen atom or asubstituent; n represents 0 (zero) or an integer of 1 to 4, with theproviso that R₇s may be the same or different independently, or R₇s maybond with each other to form a condensed ring, when n is 2 or more; orR₇ may bond with R₅ or R₆ to form a condensed ring, when n is 1 or more.9. The azomethine dye compound as claimed in claim 8, wherein, in theazomethine dye compound represented by formula (IIA), Q is a residuethat forms, together with the —N—C═N— moiety, a 4-pyrimidone ring. 10.The azomethine dye compound as claimed in claim 7, wherein theazomethine dye compound represented by formula (II) is represented byformula (IIB):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R₁ represents a methylenegroup, a methine group, or a carbon atom; r represents an integer of 1to 30, and R₁s may be the same or different independently, when r is 2or more; R₄ represents a substituent except for a hydrogen atom; mrepresents an integer of 1 to 30, and R₄s may be the same or differentindependently, or R₄S may be combined together to form a multiple bond,or alternatively R₄s may bond with each other to form a ring, when m is2 or more; X represents an aryl group; and the —(R₁)_(r)—(R₄)_(m) groupdoes not represent a straight-chain alkyl group; R₅ and R₆ eachrepresent a hydrogen atom or a substituent, or R₅ and R₆ may bond witheach other to form a ring; R₇ represents a hydrogen atom or asubstituent; n represents 0 (zero) or an integer of 1 to 4, with theproviso that R₇s may be the same or different independently, or R₇s maybond with each other to form a condensed ring, when n is 2 or more; orR₇ may bond with R₅ or R₆ to form a condensed ring, when n is 1 or more.11. The azomethine dye compound as claimed in claim 10, wherein, in theazomethine dye compound represented by formula (IIB), Q is a residuethat forms, together with the —N—C═N— moiety, a 4-pyrimidone ring; andR₄ is a group selected from the group consisting of an alkyl group, analkenyl group, an aryl group, a heterocyclic group, a halogen atom, anamino group, a hydroxyl group, a carboxyl group, a sulfo group, anacylamino group, an alkyl- or aryl-sulfonylamino group, a carbamoylgroup, a sulfamoyl group, an acyl group, a sulfonyl group, analkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, anarylthio group, a cyano group, an alkoxy group and an aryloxy group. 12.The azomethine dye compound as claimed in claim 10, wherein, in theazomethine dye compound represented by formula (IIB), at least one R₄bonds with a carbon atom at at least one α- to δ-positions in the(R₁)_(r).
 13. The dye-forming coupler as claimed in claim 1, wherein Qrepresents a residue that forms, together with the —N—C═N moiety, anitrogen-containing 6-membered ring, wherein the members of thenitrogen-containing 6-membered ring are selected from the groupconsisting of nitrogen and carbon.
 14. The azomethine dye compound asclaimed in claim 7, wherein Q represents a residue that forms, togetherwith the —N—C═N moiety, a nitrogen-containing 6-membered ring, whereinthe members of the nitrogen-containing 6-membered ring are selected fromthe group consisting of nitrogen and carbon.
 15. A compound representedby formula (I):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R_(A) represents an arylgroup, a heterocyclic group, or an (R₁)_(r)—(R₄)_(m) group; X representsan aryl group; Y represents a hydrogen atom, or a group that is capableof being split-off upon a coupling reaction with an, oxidized product ofa developing agent: wherein, when R_(A) represents an —(R₁)_(r)—(R₄)_(m)group, R₁ represents a methylene group, a methine group, or a carbonatom; r represents an integer of 1 to 30, and R₁s may be the same ordifferent independently, when r is 2 or more; R₄ represents asubstituent except for a hydrogen atom; m represents an integer of 1 to30, and R₄s may be the same or different independently, or R₄s may becombined together to form a multiple bond, or alternatively R₄s may bondwith each other to form a ring, when m is 2 or more; and the —(R₁)r—(R₄)_(m) group does not represent a straight-chain alkyl group. 16.The compound as claimed in claim 15, wherein the compound represented byformula (I) is represented by formula (IA):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R₁₁ represents an arylgroup or a heterocyclic group; X represents an aryl group; Y representsa hydrogen atom, or a group that is capable of being split-off upon acoupling reaction with an oxidized product of a developing agent. 17.The compound as claimed in claim 16, wherein, in the compoundrepresented by formula (IA), Q is a residue that forms, together withthe —N—C═N moiety, a 4-pyrimidone ring.
 18. The compound as claimed inclaim 15, wherein the compound represented by formula (I) is representedby formula (IB):

wherein Q represents a residue that forms, together with the —N—C═N—moiety, a nitrogen-containing 6-membered ring; R₁ represents a methylenegroup, a methine group, or a carbon atom; r represents an integer of 1to 30, and R₁s may be the same or different independently, when r is 2or more; R₄ represents a substituent except for a hydrogen atom; mrepresents an integer of 1 to 30, and R₄S may be the same or differentindependently, or R₄S may be combined together to form a multiple bond,or alternatively R₄s may bond with each other to form a ring, when m is2 or more; X represents an aryl group; Y represents a hydrogen atom, ora group that is capable of being split-off upon a coupling reaction withan oxidized product of a developing agent; and the —(R₁)_(r)—(R₄)_(m)group does not represent a straight-chain alkyl group.
 19. The compoundas claimed in claim 18, wherein, in the compound represented by formula(IB), Q is a residue that forms, together with the —N—C═N moiety, a4-pyrimidone ring; and R₄ is a group selected from the group consistingof an alkyl group, an alkenyl group, an aryl group, a heterocyclicgroup, a halogen atom, an amino group, a hydroxyl group, a carboxylgroup, a sulfo group, an acylamino group, an alkyl- or arylsulfonylaminogroup, a carbamoyl group, a sulfamoyl group, an acyl group, a sulfonylgroup, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylthiogroup, an arylthio group, a cyano group, an alkoxy group and an aryloxygroup.
 20. The compound as claimed in claim 18, wherein, in the compoundrepresented by formula (II), at least one R₄ bonds with a carbon atom atat least one α- to δ-positions in the (R₁)_(r).
 21. The compound asclaimed in claim 15, wherein Q represents a residue that forms, togetherwith the —N—C═N moiety, a nitrogen-containing 6-membered ring, whereinthe members of the nitrogen-containing 6-membered ring are selected fromthe group consisting of nitrogen and carbon.